Method for preparing and preserving sanitized products

ABSTRACT

Described herein are methods of sanitizing and preserving produce and other agricultural products, for example for consumption as Ready-to-Eat. The methods can comprise treating the products with a sanitizing agent and forming a protective coating over the products.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. application Ser. No.16/692,814, filed Nov. 22, 2019, which is a continuation of U.S.application Ser. No. 16/121,518, filed Sep. 4, 2018, issued as U.S. Pat.No. 10,537,115, which is a continuation of U.S. application Ser. No.15/669,304, filed Aug. 4, 2017, issued as U.S. Pat. No. 10,092,014,which is a continuation of International Application No.PCT/US2017/014978, filed Jan. 25, 2017, which claims the benefit of U.S.Provisional Application No. 62/287,170, filed Jan. 26, 2016.

TECHNICAL FIELD

The present disclosure relates to formulations and methods for treatingagricultural products, such as produce, such that the products are bothsanitized and preserved.

BACKGROUND

Common agricultural products such as fresh produce are highlysusceptible to degradation and decomposition (i.e., spoilage) whenexposed to the environment. The degradation of the agricultural productscan occur via abiotic means as a result of evaporative moisture lossfrom an external surface of the agricultural products to the atmosphereand/or oxidation by oxygen that diffuses into the agricultural productsfrom the environment and/or mechanical damage to the surface and/orlight-induced degradation (i.e., photodegradation). Furthermore, bioticstressors such as, for example, bacteria, fungi, viruses, and/or pestscan also infest and decompose the agricultural products.

Prior to being consumed, agricultural products are typically washed(e.g., soaked or rinsed in water) to remove dust, dirt, pesticides,and/or bacteria that may be harmful if consumed. While washing can occurprior to packaging of the agricultural products for subsequent sale,washing processes typically accelerate the degradation and spoilage ofthe agricultural products. As such, many agricultural products are bestpreserved and maintained in a fresh state without spoilage if they arenot washed prior to purchase, but are instead washed by consumers afterpurchase and just prior to consumption.

In recent years, there has been a push towards production of producethat is “Ready-to-Eat” (also referred to as “RTE”) without requiringwashing or other preparation by the consumer. Prior to being displayedfor sale, Ready-to-Eat produce must be washed/cleaned and sanitized inorder to lower pathogen concentrations to levels that ensure that aconsumer will not be in danger of contracting illnesses or death.However, similar to washing procedures, many methods for safesanitization of agricultural products also accelerate the degradationand spoilage of the products, as well as inducing damage. As such,methods for preparing Ready-to-Eat produce require processes thatsanitize the produce in a manner that is both safe for consumption andwhich does not substantially degrade the quality of the produce or causeit to spoil prematurely.

SUMMARY

Described herein are methods of preparing produce and other agriculturalproducts for consumption, for example as Ready-to-Eat. The methods serveboth to sanitize the agricultural products and also to preserve theproducts and extend their shelf life so that they remain fresh and can,for example, be designated as Ready-to-Eat, without causing mechanicaldamage to or substantially affecting the taste, odor, or appearance ofthe products.

Accordingly, in one aspect, a method of sanitizing and preservingproduce includes providing a solution comprising water, a sanitizingagent, and a coating agent, wherein the coating agent comprises aplurality of monomers, oligomers, fatty acids, esters, amides, amines,thiols, carboxylic acids, ethers, aliphatic waxes, alcohols, salts(inorganic and organic), or combinations thereof (herein referred to as“coating components”). In some embodiments, the coating agent comprisesa compound of Formula I. The solution is applied to a surface of theproduce for a time sufficient to sanitize the produce. At least aportion of the water and the sanitizing agent are removed from thesurface of the produce, and at least a portion of the coating agentremains on the surface of the produce as a protective coating after thewater and the sanitizing agent are at least partially removed.

In another aspect, a method of treating edible produce includesproviding a solution comprising a coating agent dissolved in a solvent,where the coating agent includes a plurality of monomers, oligomers,fatty acids, esters, amides, amines, thiols, carboxylic acids, ethers,aliphatic waxes, alcohols, salts, or combinations thereof, and thesolvent comprises water and ethanol, wherein the solvent is between 50%and 90% ethanol by volume. The solution is applied to a surface of theedible produce for a time sufficient for the solvent to sanitize theproduce and to cause a protective coating to be formed over the surfaceof the produce from the coating agent. The solvent is then at leastpartially removed from the surface of the edible produce.

In yet another aspect, a method of treating produce with a sanitizingsolution is described, where the sanitizing solution includes a coatingagent dissolved in a solvent, and the solvent includes a sanitizingagent. The sanitizing solution is applied to a surface of the produceand is allowed to contact the surface of the produce for a time periodsufficient for the sanitizing agent to reduce bacteria levels on thesurface of the produce. The solvent is then allowed to at leastpartially evaporate, thereby causing a protective coating to form fromthe coating agent over the surface of the produce.

In still another aspect, a method of treating produce includes providinga solution comprising a coating agent dissolved in a solvent, thesolvent comprising a sanitizing agent. The solution is applied to asurface of the produce to sanitize the produce, and the solvent is thenat least partially removed from the surface of the produce, causing aprotective coating to be formed from the coating agent over the surfaceof the produce.

In still another aspect, a method of treating an edible product such asproduce includes providing a solution comprising a non-sanitizingcoating agent dissolved in a solvent, wherein the solvent comprises asanitizing agent. The solution is applied to a surface of the edibleproduct, thereby allowing the solvent to sanitize the edible product.The solvent is then removed from the surface of the edible product, anda protective coating is formed from the non-sanitizing coating agentover the surface of the edible product.

Methods described herein can each include one or more of the followingfeatures, either alone or in any combination. A protective coatingformed from the coating agent can serve to prevent damage to the produceor edible product caused by the sanitizing agent, or to replace orreinforce portions of the produce or edible product which are damaged bythe sanitizing agent. The protective coating can further serve toincrease the shelf life of the produce or edible product. The protectivecoating can serve to reduce a mass loss rate of the produce or edibleproduct. The coating agent can form an edible coating over the produceor edible product. The solution can comprise between 50% and 90% ethanolby volume or between 60% and 80% ethanol by volume. The produce oredible product can be a thin skin fruit or vegetable, a berry, a grape,or an apple. In some embodiments, the coating agent includes at leastone of monomers, oligomers, fatty acids, esters, amides, amines, thiols,carboxylic acids, ethers, aliphatic waxes, alcohols, or salts. Themonomers, oligomers, fatty acids, esters, amides, amines, thiols,carboxylic acids, ethers, aliphatic waxes, alcohols, salts, orcombinations thereof can be derived from plant matter. The monomers,oligomers, fatty acids, esters, amides, amines, thiols, carboxylicacids, ethers, aliphatic waxes, alcohols, salts, or combinations thereofcan be derived from cutin.

In some embodiments of any of the above-aspects, the solvent cancomprise water. In some embodiments of any of the above-aspects, thesanitizing agent is ethanol (e.g., dissolved in water). In someembodiments, the solvent contains at least 30% ethanol (e.g., at least30%, at least 35%, at least 40%, at least 45%, at least 50%, at least55%, at least 60%, at least 65%, at least 70%, at least 75%, at least80%, at least 85%, at least 90%, or at least 95%). In some embodiments,the coating agents described herein (e.g., compounds of Formula I) areinsufficient to sanitize the edible substrate alone. In someembodiments, sanitizing the edible substrate comprises preventing fungalgrowth on the edible substrate.

The sanitizing agent can comprise ethanol, methanol, acetone,isopropanol, ethyl acetate, or combinations thereof. A volume ratio ofthe sanitizing agent to water in the solution can be in a range of about1 to 10. The monomers, oligomers, fatty acids, esters, amides, amines,thiols, carboxylic acids, ethers, aliphatic waxes, alcohols, salts, orcombinations thereof can comprise one or more compounds of Formula I:

wherein:

-   -   R is selected from —H, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆        alkynyl, —C₃-C₇ cycloalkyl, aryl, or heteroaryl, wherein each        alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or heteroaryl is        optionally substituted with one or more C₁-C₆ alkyl or hydroxy;    -   R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹² and R¹³ are each        independently, at each occurrence, —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,        halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl, —C₃-C₇        cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl,        alkynyl, cycloalkyl, aryl, or heteroaryl is optionally        substituted with one or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, or halogen;    -   R³, R⁴, R⁷ and R⁸ are each independently, at each occurrence,        —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, halogen, —C₁-C₆ alkyl, —C₂-C₆        alkenyl, —C₂-C₆ alkynyl, —C₃-C₇ cycloalkyl, aryl, or heteroaryl,        wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or        heteroaryl is optionally substituted with —OR¹⁴, —NR¹⁴R¹⁵,        —SR¹⁴, or halogen; or    -   R³ and R⁴ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring heterocycle; and/or    -   R⁷ and R⁸ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring;    -   R¹⁴ and R¹⁵ are each independently, at each occurrence, —H,        —C₁-C₆ alkyl, —C₂-C₆ alkenyl, or —C₂-C₆ alkynyl;    -   the symbol        represents an optionally single or cis or trans double bond;    -   n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;    -   m is 0, 1, 2, or 3;    -   q is 0, 1, 2, 3, 4, or 5; and    -   r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

The monomers, oligomers, fatty acids, esters, amides, amines, thiols,carboxylic acids, ethers, aliphatic waxes, alcohols, salts, orcombinations thereof can comprise monoacylglycerides. The solution canbe applied to the surface of the produce or edible product for between 1and 3,600 seconds. Sanitizing the produce or edible product can resultin reduced bacteria, viral, or fungal levels on the surface of theproduce or edible product. The steps of sanitizing the produce andforming the protective coating over the surface of the produce canresult in the produce being Ready-to-Eat. The steps of sanitizing theproduce or edible product and forming the protective coating over thesurface of the produce or edible product can result in an increase inthe shelf life of the produce or edible product as compared to untreatedproduce or edible products. A concentration of the coating agentdissolved in the solution can be in a range of about 0.1 mg/mL to 200mg/mL or 0.5 mg/mL to 200 mg/mL. The step of sanitizing the produce oredible product can further comprise sterilizing the produce or edibleproduct.

At least partially removing of the solvent from the surface of theproduce or edible product can comprise removing at least 90% of thesolvent from the surface of the produce or edible product. Applying thesolution to the surface of the produce or edible product can comprisedipping the produce or edible product in the solution or spraying thesolution on the surface of the produce or edible product. The solventcan include at least one of ethanol and water. The sanitizing agent caninclude at least one of ethanol, methanol, acetone, isopropanol, andethyl acetate. The coating agent can be formulated to prevent damage tothe produce or edible product caused by the sanitizing agent. Thecoating agent can be formulated such that the protective coating reducesa rate of water loss from the produce or edible product. The sanitizingagent can be ethanol, and the sanitizing solution can include at least30% ethanol by volume, between about 50% and about 90% ethanol byvolume, or between 60% and 80% ethanol by volume. The coating agent caninclude monoacylglycerides. The time period can be in a range of 1second to 3,600 seconds or a range of 5 seconds to 600 seconds. Thetreated produce can be labeled as Ready-to-Eat.

The coating agent can comprise a plurality of monomers, oligomers, fattyacids, esters, amides, amines, thiols, carboxylic acids, ethers,aliphatic waxes, alcohols, salts, or combinations thereof. The coatingagent can be a non-sanitizing coating agent. The solvent can furthercomprise water. The sanitizing agent can comprise an alcohol. Thesanitizing agent can comprise ethanol, methanol, acetone, isopropanol,or ethyl acetate. Sanitizing the produce or edible product can result ina reduction in a rate of fungal growth on the produce or edible product,or in an increase in the shelf life of the produce or edible productprior to fungal growth.

As used herein, “plant matter” refers to any portion of a plant, forexample, fruits (in the botanical sense, including fruit peels and juicesacs), leaves, stems, barks, seeds, flowers, or any other portion of theplant.

As used herein, a “coating agent” refers to a chemical formulation thatcan be used to coat the surface of a substrate (e.g., after removal of asolvent in which the coating agent is dispersed). The coating agent cancomprise one or more coating components. For example, the coatingcomponents can be compounds of Formula I, or monomers or oligomers ofcompounds of Formula I. Coating components can also comprise fattyacids, fatty acid esters, fatty acid amides, amines, thiols, carboxylicacids, ethers, aliphatic waxes, alcohols, salts (inorganic and organic),or combinations thereof.

As used herein, the term “sanitizing” or “sanitize” is understood tomean a chemical process that lessens or kills microorganisms (e.g.,germs) on a surface (e.g., the surface of produce), for example to makethe surface (e.g., of the produce) safe to eat. In some embodiments,sanitizing kills or removes most of the microorganisms on a surface. Forinstance, sanitizing can kill or remove at least 95%, at least 98%, atleast 99%, at least 99.99%, or at least 99.9999% of microorganisms on asurface. In some embodiments, sanitization of produce is sufficient tomake the produce ready to eat.

As used herein, “sterilizing” or “disinfecting” is understood to meanthe removal of substantially all microorganisms on a surface (e.g., thesurface of produce). In some embodiments, sanitization can comprisesterilizing or disinfecting the piece of produce. In some embodiments,sterilization or disinfection of produce is sufficient to make theproduce ready to eat. In some embodiments, the act of sanitizing a pieceof produce comprises sterilizing the produce. In some embodiments of themethods described herein, the process can both sanitize and sterilizethe produce treated.

As used herein, the term “non-sanitizing” is understood to bedescriptive of a compound, coating, formulation, or the like which isincapable of or does not sanitize objects or surfaces with which itcomes into contact. For example, a “non-sanitizing coating agent” refersto a coating agent having a chemical composition which does notindependently sanitize a surface to which the coating agent is appliedand/or over which a coating is formed from the coating agent. In someembodiments, a solution including a non-sanitizing coating agent as asolute is operable to sanitize a surface to which it is applied when thesolvent in which the solute is dissolved includes or is formed of asanitizing agent.

As used herein, the term “about” and “approximately” generally mean plusor minus 10% of the value stated, e.g., about 250 μm would include 225μm to 275 μm, about 1,000 μm would include 900 μm to 1,100 μm.

As used herein, the term “alkyl” refers to a straight or branched chainsaturated hydrocarbon. C₁-C₆ alkyl groups contain 1 to 6 carbon atoms.Examples of a C₁-C₆ alkyl group include, but are not limited to, methyl,ethyl, propyl, butyl, pentyl, isopropyl, isobutyl, sec-butyl andtert-butyl, isopentyl and neopentyl.

As used herein, the term “alkenyl” means an aliphatic hydrocarbon groupcontaining a carbon-carbon double bond and which may be straight orbranched. Some alkenyl groups have 2 to about 4 carbon atoms in thechain. Branched means that one or more lower alkyl groups such asmethyl, ethyl, or propyl are attached to a linear alkenyl chain.Exemplary alkenyl groups include ethenyl, propenyl, n-butenyl, andi-butenyl. A C₂-C₆ alkenyl group is an alkenyl group containing between2 and 6 carbon atoms. As defined herein, the term “alkenyl” can includeboth “E” and “Z” or both “cis” and “trans” double bonds.

As used herein, the term “alkynyl” means an aliphatic hydrocarbon groupcontaining a carbon-carbon triple bond and which may be straight orbranched. Some alkynyl groups have 2 to about 4 carbon atoms in thechain. Branched means that one or more lower alkyl groups such asmethyl, ethyl, or propyl are attached to a linear alkynyl chain.Exemplary alkynyl groups include ethynyl, propynyl, n-butynyl,2-butynyl, 3-methylbutynyl, and n-pentynyl. A C₂-C₆ alkynyl group is analkynyl group containing between 2 and 6 carbon atoms.

As used herein, the term “cycloalkyl” means monocyclic or polycyclicsaturated carbon rings containing 3-18 carbon atoms. Examples ofcycloalkyl groups include, without limitations, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptanyl, cyclooctanyl, norboranyl,norborenyl, bicyclo[2.2.2]octanyl, or bicyclo[2.2.2]octenyl. A C₃-C₈cycloalkyl is a cycloalkyl group containing between 3 and 8 carbonatoms. A cycloalkyl group can be fused (e.g., decalin) or bridged (e.g.,norbornane).

As used herein, the term “aryl” refers to cyclic, aromatic hydrocarbongroups that have 1 to 2 aromatic rings, including monocyclic or bicyclicgroups such as phenyl, biphenyl or naphthyl. Where containing twoaromatic rings (bicyclic, etc.), the aromatic rings of the aryl groupmay be joined at a single point (e.g., biphenyl), or fused (e.g.,naphthyl). The aryl group may be optionally substituted by one or moresubstituents, e.g., 1 to 5 substituents, at any point of attachment.

As used herein, the term “heteroaryl” means a monovalent monocyclic orbicyclic aromatic radical of 5 to 12 ring atoms or a polycyclic aromaticradical, containing one or more ring heteroatoms selected from N, O, orS, the remaining ring atoms being C. Heteroaryl as herein defined alsomeans a bicyclic heteroaromatic group wherein the heteroatom(s) isselected from N, O, or S. The aromatic radical is optionally substitutedindependently with one or more substituents described herein.

As used herein, the term “halo” or “halogen” means fluoro, chloro,bromo, or iodo.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows plots of percent mass loss of blueberries versus time foruntreated blueberries and for blueberries that have been treated with asanitizing agent.

FIG. 2 illustrates a process for preparing sanitized (e.g.,Ready-to-Eat) produce.

FIG. 3 shows plots of percent mass loss of blueberries versus time foruntreated blueberries and for blueberries that have been treated with asolution including both a coating agent and a sanitizing agent.

FIG. 4 is a plot of average mass loss rates of untreated blueberries andof blueberries that have been treated with a solution including both acoating agent comprising C₁₆ glycerol esters and a sanitizing agent.

FIG. 5 is a plot of average mass loss rates of untreated blueberries andof blueberries that have been treated with a solution including both acoating agent comprising Cis glycerol esters and a sanitizing agent.

FIG. 6 is a plot of the percent mass loss of blueberries as a functionof time.

FIG. 7 shows high resolution photographs of treated and untreatedblueberries.

FIG. 8 is a plot of average mass loss rates of untreated strawberriesand of strawberries that have been treated with a solution includingboth a coating agent comprising C₁₆ glycerol esters and a sanitizingagent.

FIG. 9 shows high resolution time lapse photographs of treated anduntreated strawberries.

FIGS. 10-12 are plots of the shelf life factor of groups of avocadosthat have each been treated with a solution including both a coatingagent and a sanitizing agent.

FIGS. 13A-13B are high resolution photographs of treated pomegranates.

FIGS. 14A-14B are high resolution photographs of treated limes.

FIG. 15A shows a photo of Colletotrichum spores after incubation on aslide coated with a composition of the present disclosure.

FIG. 15B shows a photo of Botrytis spores after incubation on a slidecoated with a composition of the present disclosure.

FIGS. 16A-16G show photos of Colletotrichum spores after incubation onslides coated with fruit wax and after treatment with variousconcentrations of ethanol and water.

FIGS. 17A-17C show photos of Colletotrichum spores after incubation onslides coated with fruit wax and after treatment with variousconcentrations of ethanol and water in the presence of a coatingcomposition of the present disclosure.

FIGS. 18A-18G show photos of Botrytis spores after incubation on slidescoated with fruit wax and after treatment with various concentrations ofethanol and water.

FIGS. 19A-19C show photos of Botrytis spores after incubation on slidescoated with fruit wax and after treatment with various concentrations ofethanol and water in the presence of a coating composition of thepresent disclosure.

FIGS. 20A-20D show photos of Penicillium spores after incubation onslides coated with fruit wax and after treatment with variousconcentrations of ethanol and water.

FIGS. 21A-21B show photos of Penicillium spores after incubation onslides coated with fruit wax and after treatment with variousconcentrations of ethanol and water in the presence of a coatingcomposition of the present disclosure.

FIG. 22 is a table listing percent germination of Penicillium sporesafter incubation on slides coated with fruit wax and after treatmentwith solutions of the present disclosure.

DETAILED DESCRIPTION

Described herein are methods of preparing produce and other products forconsumption, for example as Ready-to-Eat. The methods serve both tosanitize the products and also to preserve the products and extend theirshelf life so that they remain fresh and can, for example, be designatedas Ready-to-Eat produce, without causing mechanical damage to orsubstantially affecting the taste, odor, or appearance of the products.The methods generally include treating the surface of the product with asolution which includes a composition of monomers, oligomers, fattyacids, esters, amides, amines, thiols, carboxylic acids, ethers,aliphatic waxes, alcohols, salts (inorganic and organic), orcombinations thereof (coating components) dissolved in a solvent, thesolvent including a sanitizing agent. In some embodiments, thesanitizing agent is ethanol. The solution is applied to the surface ofthe product for a time sufficient for the sanitizing agent to sanitizethe surface of the product, after which the solvent is removed from thesurface, for example by evaporation, blowing with fans, heating,toweling, or combinations thereof. Application of the solution to thesurface further results in a protective coating being formed on thesurface from the coating components, as further described below. In someembodiments in which the product is produce, the protective coating,which remains on the surface after the solvent is removed, preventsdamage to the surface caused by the solvent and results in an increasein the shelf life of the produce as compared to similar produce whichhas been harvested but is otherwise untreated. In other embodiments inwhich the product is produce, the protective coating remains on thesurface after the solvent is removed and replaces and/or reinforcesportions of the natural coating covering of the produce (e.g., thecuticular layer) which are damaged by the solvent, thereby mitigating oreliminating the deleterious effects the solvent has on the surface, andin some cases improving the ability of the produce to preventpost-harvest water loss, oxidation, or other forms of degradation. Thecomposition of the coating components can be formulated such that thecoating is both edible and substantially undetectable. As such, coatedagricultural products can, for example, be packaged and sold asReady-to-Eat.

Many agricultural products such as fresh-cut fruits and vegetables areconsumed without being cooked, thereby causing a risk to the consumer ofillness caused by pathogen contamination. In recent years, a number ofoutbreaks have been traced to agricultural products processed underconditions that were not sufficiently sanitary. Direct sanitization ofpost-harvest (and in some cases pre-harvest) agricultural products istypically performed in order to minimize the risk of such contamination.Furthermore, many agricultural products are prone to molding or otherdegradation by biotic stressors during storage and/or shipping. Forexample, many agricultural products are shipped over long geographicaldistances from the growers' locations to the sellers' locations, oftenrequiring them to be stored for extended periods of time during shipping(e.g., 30 days or longer). In order to prevent or mitigate water andmass loss from the products during shipping, the products are typicallyshipped in a high relative humidity atmosphere (e.g., 90% or 95%relative humidity). While such high relative humidity conditions areeffective at reducing the rate of mass loss from the products, they alsocreate an environment ideally suited for fungal and other microbialgrowth. Sanitizing the agricultural products prior to storing andshipping can reduce the rate of molding or other microbialcontamination. However, it is important that the sanitization processcauses little or no physical damage to the surface of the products, doesnot adversely impact the taste of the products, and does not leaveharmful residuals on the products.

In the case of Ready-to-Eat agricultural products, in order for theproducts to be marketed and sold as Ready-to-Eat, they need to besanitized prior to packaging. The sanitization process is preferably onethat causes little or no physical damage to the products. Furthermore,after sanitization and packaging, the products need to remain freshuntil they are sold and consumed.

Common chemical methods for cleaning and sanitizing agricultural andother food products typically include application of mechanical washingin the presence of a sanitizing agent such as peracetic acid, chlorine,chlorine dioxide, calcium hypochlorite, or sodium hypoclorite. However,many of these sanitizing agents present other safety concerns whenresidual concentrations that remain on the food products are too high.

Other solvents such as ethanol, methanol, acetone, isopropanol, andethyl acetate are known to be effective sanitizing agents, andagricultural products treated with these agents can be sufficientlysanitized so as to be safe for consumption. At least some of thesesolvents (e.g., ethanol) are also safe for consumption in much higherconcentrations than many of the sanitizing agents typically used tosanitize agricultural and food products. However, a problem arises inthat these sanitizing agents typically damage the agricultural productsand substantially reduce their shelf life, particularly in the case ofthin skinned fruits and vegetables such as berries and grapes, as wellas produce that has been cut to expose an inner surface. For example, asdetailed below with reference to FIG. 1 , treating harvested producesuch as blueberries with ethanol typically causes an increase in therate of mass loss of the produce. While such problems can in some casesbe partially mitigated by diluting the sanitizing agent(s) in water,solutions for which the sanitizing agent is less than about 30% byvolume, for example less than about 50% by volume, may not be effectiveat sufficiently sanitizing the agricultural product, for example toenable its use in Ready-to-Eat applications. Furthermore, asdemonstrated below, solutions for which any of the above sanitizingagents is greater than 50% (and typically greater than 30%) by volumetend to damage the surface of the agricultural products and/orsubstantially reduce their shelf life.

In many cases, the damage caused to produce by sanitizing agents appliedto the surface of the produce results in an increase in the rate ofpost-harvest mass loss. This occurs because the sanitizing agent canremove or damage at least a portion of the produce's natural barrier towater loss (e.g., the cuticular layer that covers the produce). Forexample, FIG. 1 shows plots of percent mass loss of blueberries versustime. The blueberries were all harvested simultaneously and divided intogroups, each of the groups being qualitatively identical to the othergroups (i.e., all groups had blueberries of approximately the sameaverage size and quality). The first group of blueberries (correspondingto 102 in FIG. 1 ) was not washed or treated in any way, the secondgroup (corresponding to 104 in FIG. 1 ) was treated in a 1:1 mixture ofethanol and water, the third group (corresponding to 106 in FIG. 1 ) wastreated in a 3:1 mixture of ethanol and water, and the fourth group(corresponding to 108 in FIG. 1 ) was treated in substantially pureethanol. As shown in FIG. 1 , the untreated blueberries exhibited asubstantially lower rate of mass loss during the four days afterharvesting as compared to the blueberries that had been subjected toethanol or to ethanol/water mixtures. Specifically, after just underfour days, the untreated blueberries (102) experienced an averagepercent mass loss of about 15.4%, the blueberries treated in the 1:1mixture of ethanol and water (104) experienced an average percent massloss of about 17.4%, the blueberries treated in the 3:1 mixture ofethanol and water (106) experienced an average percent mass loss ofabout 17.7%, and the blueberries treated in substantially pure ethanol(108) experienced an average percent mass loss of about 19%.

FIG. 3 shows plots of percent mass loss of blueberries versus time forboth untreated blueberries (plot 302, which is the same as plot 102shown in FIG. 1 ) and for blueberries treated with solutions includingboth a sanitizing agent and a coating agent (plots 308 and 306), as inthe method described below. The first group of blueberries(corresponding to 302 in FIG. 3 ) was not washed or treated in any way,the second group (corresponding to 308 in FIG. 3 ) was treated in asolution including a coating agent dissolved in substantially pureethanol, and the third group (corresponding to 306 in FIG. 3 ) wastreated in a solution including a coating agent dissolved in a 9:1mixture of ethanol and water (i.e., 90% ethanol, 10% water). For bothplots 308 and 306, the coating agent included a 3:1 mixture (by mass) of1,3-dihydroxypropan-2-yl hexadecanoate (2-monoacylglycerides) and2,3-dihydroxypropan-1-yl hexadecanoate (1-monoacylglycerides) dissolvedin the solvent at a concentration of 10 mg/mL.

As shown in FIG. 3 , the blueberries treated with solutions includingboth a sanitizing agent and a coating agent exhibited a substantiallylower rate of mass loss during the four days after harvesting ascompared to the untreated blueberries. This was unexpected in that it isexactly opposite to the trend illustrated in FIG. 1 , for whichblueberries treated with solutions including the sanitizing agent butnot the coating agent exhibited substantially higher rates of mass lossthan untreated blueberries. Accordingly, in some embodiments, thecoatings of the present disclosure can mitigate and in some casesreverse the detrimental effects of sanitizing agents (e.g., ethanol).Referring again to FIG. 3 , after just under four days, the untreatedblueberries (302) experienced an average percent mass loss of about15.4%, the blueberries treated in the solution including the coatingagent dissolved in substantially pure ethanol (308) experienced anaverage percent mass loss of about 11.8%, and the blueberries treated inthe solution including the coating agent dissolved in the 9:1 mixture ofethanol and water (306) experienced an average percent mass loss ofabout 10.6%.

FIG. 4 , which examines the effect of various compositions of C₁₆glycerol esters, is a graph showing average daily mass loss rates forblueberries, measured over the course of several days, where theblueberries were treated with a solution including a coating agent and asanitizing agent. The coating agents included various mixtures of1,3-dihydroxypropan-2-yl hexadecanoate and 2,3-dihydroxypropan-1-ylhexadecanoate, as detailed below. Each bar in the graph representsaverage daily mass loss rates for a group of 60 blueberries. Theblueberries corresponding to bar 402 were untreated (control group). Theblueberries corresponding to bar 404 were treated with a solution forwhich the coating agent was substantially pure 2,3-dihydroxypropan-1-ylhexadecanoate. The blueberries corresponding to bar 406 were treatedwith a solution for which the coating agent was about 75%2,3-dihydroxypropan-1-yl hexadecanoate and 25% 1,3-dihydroxypropan-2-ylhexadecanoate by mass. The blueberries corresponding to bar 408 weretreated with a solution for which the coating agent was about 50%2,3-dihydroxypropan-1-yl hexadecanoate and 50% 1,3-dihydroxypropan-2-ylhexadecanoate by mass. The blueberries corresponding to bar 410 weretreated with a solution for which the coating agent was about 25%2,3-dihydroxypropan-1-yl hexadecanoate and 75% 1,3-dihydroxypropan-2-ylhexadecanoate by mass. The blueberries corresponding to bar 412 weretreated with a solution for which the coating agent was substantiallypure 1,3-dihydroxypropan-2-yl hexadecanoate. The coating agents wereeach dissolved in substantially pure ethanol (sanitizing agent) at aconcentration of 10 mg/mL to form the solution, and the solution wasapplied to the surfaces of the blueberries to sanitize the surfaces andto form coatings.

As shown in FIG. 4 , the untreated blueberries (402) exhibited anaverage mass loss rate of nearly 2.5% per day, which was more than theblueberries treated with a coating agent and sanitizing agent of thepresent disclosure. The lowest percent mass loss was seen in blueberriescoated with 25% 2,3-dihydroxypropan-1-yl hexadecanoate and 75%1,3-dihydroxypropan-2-yl hexadecanoate. The mass loss rates of theblueberries treated with the substantially pure 2,3-dihydroxypropan-1-ylhexadecanoate formulation (404) and the substantially pure1,3-dihydroxypropan-2-yl hexadecanoate formulation (412), as well as theblueberries corresponding to bars 406 (2,3-dihydroxypropan-1-ylhexadecanoate to 1,3-dihydroxypropan-2-yl hexadecanoate mass ratio ofabout 3) and 408 (2,3-dihydroxypropan-1-yl hexadecanoate to1,3-dihydroxypropan-2-yl hexadecanoate mass ratio of about 1) exhibitedaverage daily mass loss rates between 2.1% and 2.3%, which was better(lower) than the untreated blueberries (402). The blueberriescorresponding to bar 410 (2,3-dihydroxypropan-1-yl hexadecanoate to1,3-dihydroxypropan-2-yl hexadecanoate mass ratios of about 0.33)exhibited mass loss rates under 2%, which was a substantial improvementover the untreated blueberries (402).

FIG. 5 , which examines the effect of various compositions of Cisglycerol esters, is a graph showing average daily mass loss rates forblueberries, measured over the course of several days, where theblueberries were treated with a solution including a coating agent and asanitizing agent. The coating agents included various mixtures of1,3-dihydroxypropan-2-yl octadecanoate and 2,3-dihydroxypropan-1-yloctadecanoate, as detailed below. Each bar in the graph representsaverage daily mass loss rates for a group of 60 blueberries. Theblueberries corresponding to bar 502 were untreated (control group). Theblueberries corresponding to bar 504 were treated with a solution forwhich the coating agent was substantially pure 2,3-dihydroxypropan-1-yloctadecanoate. The blueberries corresponding to bar 506 were treatedwith a solution for which the coating agent was 75%2,3-dihydroxypropan-1-yl octadecanoate and 25% 1,3-dihydroxypropan-2-yloctadecanoate by mass. The blueberries corresponding to bar 508 weretreated with a solution for which the coating agent was 50%2,3-dihydroxypropan-1-yl octadecanoate and 50% 1,3-dihydroxypropan-2-yloctadecanoate by mass. The blueberries corresponding to bar 510 weretreated with a solution for which the coating agent was 25%2,3-dihydroxypropan-1-yl octadecanoate and 75% 1,3-dihydroxypropan-2-yloctadecanoate by mass. The blueberries corresponding to bar 512 weretreated with a solution for which the coating agent was substantiallypure 1,3-dihydroxypropan-2-yl octadecanoate. The coating agents wereeach dissolved in substantially pure ethanol (sanitizing agent) at aconcentration of 10 mg/mL to form the solution, and the solution wasapplied to the surfaces of the blueberries to sanitize the surfaces andto form coatings.

As shown in FIG. 5 , the results for 2,3-dihydroxypropan-1-yloctadecanoate/1,3-dihydroxypropan-2-yl octadecanoate coating agentmixtures were similar to those for 2,3-dihydroxypropan-1-ylhexadecanoate/1,3-dihydroxypropan-2-yl hexadecanoate coating agentmixtures in FIG. 4 . The untreated blueberries (502) exhibited anaverage mass loss rate of about 2.4% per day, which was higher thanblueberries coated with a composition of the present disclosure. Thelowest percent mass loss was seen in blueberries coated with 25%2,3-dihydroxypropan-1-yl octadecanoate and 75% 1,3-dihydroxypropan-2-yloctadecanoate. The mass loss rates of the blueberries treated with thesubstantially pure 2,3-dihydroxypropan-1-yl octadecanoate formulation(504) and the substantially pure 1,3-dihydroxypropan-2-yl octadecanoateformulation (512), as well as the blueberries corresponding to bars 506(2,3-dihydroxypropan-1-yl octadecanoate to 1,3-dihydroxypropan-2-yloctadecanoate mass ratio of about 3) and 508 (2,3-dihydroxypropan-1-yloctadecanoate to 1,3-dihydroxypropan-2-yl octadecanoate mass ratio ofabout 1) exhibited average daily mass loss rates between 2.1% and 2.2%,which was better than the untreated blueberries (502). The blueberriescorresponding to bar 510 (2,3-dihydroxypropan-1-yl octadecanoate to1,3-dihydroxypropan-2-yl octadecanoate mass ratio of about 0.33)exhibited average mass loss rates of about 1.8%, which was a substantialimprovement over the untreated blueberries (502). Accordingly, withoutwishing to be bound by theory, as set forth in FIGS. 4 and 5 ,compositions comprising 1-monoacylglycerides and/or 2-monoacylglycerides(e.g., about 25% 1-monoacylglycerides and about 75%2-monoacylglycerides) can be effective at reducing mass loss rates insanitized produce.

FIG. 6 , which examines the effect of coating agent concentration onmass loss rates, shows plots of the percent mass loss over the course of5 days in untreated blueberries (602), blueberries treated with a firstsolution of 10 mg/mL of coating agent compounds dissolved in ethanol(604), and blueberries treated with a second solution of 20 mg/mL ofcoating agent compounds dissolved in ethanol (606). The coating agentsin both the first and second solutions included a mixture of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate, where the mass ratio of 2,3-dihydroxypropan-1-ylhexadecanoate to 1,3-dihydroxypropan-2-yl hexadecanoate was 0.33. Asshown, the percent mass loss for untreated blueberries was almost 20%after 5 days, whereas the percent mass loss for blueberries treated withthe 10 mg/mL solution was less than 15% after 5 days, and the percentmass loss for blueberries treated with the 20 mg/mL solution was lessthan 10% after 5 days. Accordingly, without wishing to be bound bytheory, higher concentrations of coating agent can lead to furtherreduction in mass loss rates of sanitized produce.

FIG. 7 shows high resolution photographs of the untreated blueberries(602) from the study in FIG. 6 , and of the blueberries treated with the10 mg/mL solution of a 1:3 mass ratio of 2,3-dihydroxypropan-1-ylhexadecanoate to 1,3-dihydroxypropan-2-yl hexadecanoate (604) from thestudy of FIG. 6 , taken at day 5. The skins of the untreated blueberries602 were highly wrinkled as a result of mass loss of the blueberries,whereas the skins of the treated blueberries remained very smooth.

FIG. 8 is a graph showing average daily mass loss rates forstrawberries, measured over the course of 4 days, where the strawberrieswere treated with a solution including a coating agent and a sanitizingagent. The coating agents included various mixtures of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate, as detailed below. Each bar in the graph representsaverage daily mass loss rates for a group of 15 strawberries. Thestrawberries corresponding to bar 802 were untreated (control group).The strawberries corresponding to bar 804 were treated with a solutionfor which the coating agent was substantially pure2,3-dihydroxypropan-1-yl hexadecanoate. The strawberries correspondingto bar 806 were treated with a solution for which the coating agent was75% 2,3-dihydroxypropan-1-yl hexadecanoate and 25%1,3-dihydroxypropan-2-yl hexadecanoate by mass. The strawberriescorresponding to bar 808 were treated with a solution for which thecoating agent was 50% 2,3-dihydroxypropan-1-yl hexadecanoate and 50%1,3-dihydroxypropan-2-yl hexadecanoate by mass. The strawberriescorresponding to bar 810 were treated with a solution for which thecoating agent was 25% 2,3-dihydroxypropan-1-yl hexadecanoate and 75%1,3-dihydroxypropan-2-yl hexadecanoate by mass. The strawberriescorresponding to bar 812 were treated with a solution for which thecoating agent was substantially pure 1,3-dihydroxypropan-2-ylhexadecanoate. The coating agents were each dissolved in substantiallypure ethanol (sanitizing agent) at a concentration of 10 mg/mL to formthe solution, and the solution was applied to the surfaces of thestrawberries to sanitize the surfaces and to form coatings.

As shown in FIG. 8 , the untreated strawberries (802) exhibited anaverage mass loss rate of greater than 7.5% per day. The mass loss ratesof the strawberries treated with the substantially pure2,3-dihydroxypropan-1-yl hexadecanoate formulation (804) and thesubstantially pure 1,3-dihydroxypropan-2-yl hexadecanoate formulation(812) exhibited average daily mass loss rates between 6% and 6.5%, whichwas better than that of the untreated strawberries (802). Thestrawberries corresponding to bar 806 (2,3-dihydroxypropan-1-ylhexadecanoate to 1,3-dihydroxypropan-2-yl hexadecanoate mass ratio of 3)exhibited even lower mass loss rates, slightly less than 6% per day. Thestrawberries corresponding to bars 808 and 810 (2,3-dihydroxypropan-1-ylhexadecanoate to 1,3-dihydroxypropan-2-yl hexadecanoate mass ratios of 1and 0.33, respectively) exhibited substantially improved mass lossrates; the strawberries corresponding to bar 808 exhibited average dailymass loss rates of just over 5%, while the strawberries corresponding tobar 810 exhibited average daily mass loss rates of under 5%.

FIG. 9 shows high resolution photographs of 4 coated and 4 uncoatedstrawberries over the course of 5 days. The strawberries were kept underambient room conditions at a temperature in the range of about 23°C.-27° C. and humidity in the range of about 40%-55% for the entireduration of the time they were tested. The coated strawberries weretreated with a solution for which the coating agent was a mixture of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate combined at a mass ratio of 0.33, as in bar 810 in FIG. 8. As seen, the untreated strawberries began to exhibit fungal growth anddiscoloration by day 3, and were mostly covered in fungus by day 5. Incontrast, the treated strawberries did not exhibit any fungal growth byday 5 and were largely similar in overall color and appearance on day 1and day 5. Accordingly, without wishing to be bound by theory, as setforth in FIGS. 8 and 9 , treating produce with a solution which includesa coating agent comprising 1-monoacylglycerides and/or2-monoacylglycerides dissolved in a sanitizing agent can be effective atreducing a rate of and/or delaying the onset of fungal growth while atthe same time reducing a mass loss rate of the produce. That is, thetreatment can reduce the rate of fungal growth over the produce, and/orcan increase the shelf life of the produce prior to fungal growth, whileat the same time reducing a mass loss rate of the produce.

FIG. 10 is a graph showing the shelf life factor for avocados that wereeach treated with a solution including a coating agent dissolved inethanol (sanitizing agent). The coating agents included various mixturesof monoacylglyceride compounds, as detailed below. Each bar in the graphrepresents a group of 30 avocados and corresponds to a different coatingagent composition. Bar 1002 corresponds to 25:75 mixture of2,3-dihydroxypropan-1-yl tetradecanoate (MA1G) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G), bar 1004 corresponds to50:50 mixture of 2,3-dihydroxypropan-1-yl tetradecanoate and1,3-dihydroxypropan-2-yl hexadecanoate, bar 1006 corresponds to 75:25mixture of 2,3-dihydroxypropan-1-yl tetradecanoate and1,3-dihydroxypropan-2-yl hexadecanoate, bar 1012 corresponds to 25:75mixture of 2,3-dihydroxypropan-1-yl hexadecanoate (PA1G) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G), bar 1014 corresponds to50:50 mixture of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate, bar 1016 corresponds to 75:25mixture of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate, bar 1022 corresponds to 25:75mixture of 2,3-dihydroxypropan-1-yl octadecanoate (SA1G) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G), bar 1024 corresponds to50:50 mixture of 2,3-dihydroxypropan-1-yl octadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate, and bar 1026 corresponds to75:25 mixture of 2,3-dihydroxypropan-1-yl octadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate. The coating agents were eachdissolved in substantially pure ethanol (sanitizing agent) at aconcentration of 5 mg/mL to form the solution, and the solution wasapplied to the surfaces of the avocados to sanitize the surfaces and toform coatings. As seen in FIG. 10 , each of the treatments resulted in ashelf life factor of between 1.3 and 1.6 for the treated avocados,indicating a substantial increase in their shelf life as compared tountreated avocados.

As used herein, the term “shelf life factor” is defined as the ratio ofthe average mass loss rate of untreated produce (measured for a controlgroup) to the average mass loss rate of the corresponding treatedproduce. Hence, a shelf life factor greater than 1 corresponds to adecrease in average mass loss rate of treated produce as compared tountreated produce, and a larger shelf life factor corresponds to agreater reduction in average mass loss rate.

FIG. 11 is a graph showing the shelf life factor for avocados that wereeach treated with a solution including another coating agent dissolvedin ethanol (sanitizing agent). Each bar in the graph represents a groupof 30 avocados and corresponds to a different coating agent composition.Bar 1102 corresponds to 25:75 mixture of tetradecanoic acid (MA) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G), bar 1104 corresponds to50:50 mixture of tetradecanoic acid and 1,3-dihydroxypropan-2-ylhexadecanoate, bar 1106 corresponds to 75:25 mixture of tetradecanoicacid and 1,3-dihydroxypropan-2-yl hexadecanoate, bar 1112 corresponds to25:75 mixture of hexadecanoic acid (PA) and 1,3-dihydroxypropan-2-ylhexadecanoate (PA2G), bar 1114 corresponds to 50:50 mixture ofhexadecanoic acid and 1,3-dihydroxypropan-2-yl hexadecanoate, bar 1116corresponds to 75:25 mixture of hexadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate, bar 1122 corresponds to 25:75mixture of octadecanoic acid (SA) and 1,3-dihydroxypropan-2-ylhexadecanoate (PA2G), bar 1124 corresponds to 50:50 mixture ofoctadecanoic acid and 1,3-dihydroxypropan-2-yl hexadecanoate, and bar1126 corresponds to 75:25 mixture of octadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate. The coating agents were eachdissolved in substantially pure ethanol (sanitizing agent) at aconcentration of 5 mg/mL to form the solution, and the solution wasapplied to the surfaces of the avocados to sanitize the surfaces and toform coatings. As seen in FIG. 11 , each of the treatments resulted in ashelf life factor of between 1.25 and 1.55 for the treated avocados,indicating a substantial increase in their shelf life as compared tountreated avocados.

FIG. 12 is a graph showing the shelf life factor for avocados that wereeach treated with a solution including another coating agent dissolvedin ethanol (sanitizing agent). Each of the bars represents a group of 30avocados and corresponds to a different coating agent composition. Bars1201-1203 correspond to coating agents which are mixtures of ethylpalmitate (EtPA) and 1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)combined at a molar ratio of 25:75 (bar 1201), 50:50 (bar 1202), and75:25 (bar 1203). Bars 1211-1213 correspond to coating agents which aremixtures of oleic acid (OA) and 1,3-dihydroxypropan-2-yl hexadecanoate(PA2G) combined at a molar ratio of 25:75 (bar 1211), 50:50 (bar 1212),and 75:25 (bar 1213). Bars 1221-1223 correspond to coating agents whichare mixtures of tetradecanoic acid (MA) and 2,3-dihydroxypropan-1-yloctadecanoate (SA1G) combined at a molar ratio of 25:75 (bar 1221),50:50 (bar 1222), and 75:25 (bar 1223). Bars 1231-1233 correspond tocoating agents which are mixtures of hexadecanoic acid (PA) and2,3-dihydroxypropan-1-yl octadecanoate (SA1G) combined at a molar ratioof 25:75 (bar 1231), 50:50 (bar 1232), and 75:25 (bar 1233). Bars1241-1243 correspond to coating agents which are mixtures ofoctadecanoic acid (SA) and 2,3-dihydroxypropan-1-yl octadecanoate (SA1G)combined at a molar ratio of 25:75 (bar 1241), 50:50 (bar 1242), and75:25 (bar 1243). The coating agents were each dissolved insubstantially pure ethanol (sanitizing agent) at a concentration of 5mg/mL to form the solution, and the solution was applied to the surfacesof the avocados to sanitize the surfaces and to form coatings. As seenin FIG. 12 , each of the treatments resulted in a shelf life factor ofbetween 1.25 and 1.8 for the treated avocados, indicating a substantialincrease in their shelf life as compared to untreated avocados.

FIGS. 13A and 13B show high resolution photographs of pomegranates thatwere each treated with a solution including a coating agent dissolved ina solvent. The images are each representative of ten pomegranates thatunderwent the same treatment. In both cases, the coating agent was a30:70 mixture of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate and was dissolved in the solventat a concentration of 40 mg/mL. For FIG. 13A, the solvent was pureethanol (sanitizing agent), while for FIG. 13B, the solvent was 70%ethanol (sanitizing agent) and 30% water. For the pomegranates treatedwith the 100% ethanol solution (FIG. 13A), the solvent contacted thesurfaces of the pomegranates for about 30-60 seconds before completelyevaporating away, after which the coating agent remained on thesurfaces. For the pomegranates treated with the 70% ethanol solution(FIG. 13B), the solvent contacted the surfaces of the pomegranates forabout 10 minutes before completely evaporating away, after which thecoating agent remained on the surfaces. Visible skin breakdown wasobserved in the pomegranates treated with the 100% ethanol solution(FIG. 13A), whereas the pomegranates treated with the 70% ethanolsolution (FIG. 13B) appeared undamaged and were otherwise unaltered inappearance by the treatment.

FIGS. 14A and 14B show high resolution photographs of limes that wereeach treated with a solution including a coating agent dissolved in asolvent. The images are each representative of six limes that underwentthe same treatment. In both cases, the coating agent was a 30:70 mixtureof 2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate and was dissolved in the solvent at a concentration of 40mg/mL. For FIG. 14A, the solvent was pure ethanol (sanitizing agent),while for FIG. 14B, the solvent was 80% ethanol (sanitizing agent) and20% water. For the limes treated with the 100% ethanol solution (FIG.14A), the solvent contacted the surfaces of the limes for about 30-60seconds before completely evaporating away, after which the coatingagent remained on the surfaces. For the limes treated with the 80%ethanol solution (FIG. 14B), the solvent contacted the surfaces of thelimes for about 10 minutes before completely evaporating away, afterwhich the coating agent remained on the surfaces. Visible skin breakdownwas observed in the limes treated with the 100% ethanol solution (FIG.14A), whereas the limes treated with the 80% ethanol solution (FIG. 14B)appeared undamaged and were otherwise unaltered in appearance by thetreatment. Accordingly, without wishing to be bound by theory, as setforth in FIGS. 13A-13B and 14A-14B, treating produce with a solutionwhich includes a coating agent dissolved in a solvent which includes asanitizing agent can in some cases cause visible damage to the producewhen the concentration of the sanitizing agent is too high (e.g., whenthe solvent is 100% ethanol), while not causing visible damage to theproduce when the concentration of the sanitizing agent is lower (e.g.,when the solvent is no more than 80% or 70% ethanol by volume).

FIG. 15A and FIG. 15B show that fungal spores that are deposited ontocertain coating compositions of the present disclosure (e.g., a 30:70mixture of palmitic acid 1-glycerol and palmitic acid 2-glycerol) areable to survive and germinate. Accordingly, without wishing to be boundby theory, it is understood that at least some of the coatingcompositions of the present disclosure (for instance, in the absence ofa sanitizing agent) do not independently prevent or suppress fungalgrowth or sanitize the surface onto which they are applied. As such, atleast some of the coating agents of the present disclosure arenon-sanitizing coating agents.

FIGS. 16A-16G, 17A-17C, 18A-18G, and 19A-19C show optical microscopeimages of glass slides coated with fruit wax and treated withColletotrichum (16A-16G and 17A-17C) and Botrytis (18A-18G and 19A-19C)spores. As set forth in FIGS. 16A-16G and 18A-18G, and described in moredetails in the Examples below, spores were found to germinate even aftertreatment with ethanol compositions below 30% ethanol. However,treatment with ethanol concentrations at 30% and above was found toinhibit the germination of fungal spores. As set forth in FIGS. 17A-17Cand 19A-19C, higher ethanol concentrations were still found to inhibitthe germination of fungal spores when a coating agent of the presentdisclosure (e.g., a 30:70 mixture of palmitic acid 1-glycerol andpalmitic acid 2-glycerol) was dissolved in the ethanol (or ethanol/watermixture) and left on the surface of the coated glass slides.Accordingly, without wishing to be bound by theory, use of a sanitizingagent (e.g., ethanol) as part of the solvent can help sanitize andreduce fungal growth when applied to an edible substrate (e.g.,produce). Furthermore, without wishing to be bound by theory, ethanolsolutions at or about 30% or greater ethanol concentration can sanitizethe surface of produce and prevent microbial (e.g., fungal) growth.Moreover, without wishing to be bound by theory, when coatingcompositions of the present disclosure are included in an ethanol/watermixture of 30% or greater ethanol composition, microbial (e.g., fungal)growth is prevented.

FIGS. 20A-20D and 21A-21B show optical microscope images of glass slidescoated with fruit wax and treated with Penicillium spores. FIG. 22 is atable showing percent germination of Penicillium spores for each of theconditions corresponding to FIGS. 20A-20D and 21A-21B. Spores were foundto germinate even after treatment with ethanol compositions of 30% orless. However, treatment with higher ethanol concentrations (e.g., 70%ethanol or 100% ethanol) was found to inhibit the germination of fungalspores. As set forth in FIG. 22 , higher ethanol concentrations werestill found to inhibit the germination of Penicillium spores when acoating agent of the present disclosure (e.g., a 30:70 mixture ofstearic acid 1-glycerol and palmitic acid 2-glycerol) was dissolved inthe ethanol (or ethanol/water mixture) and left on the surface of thecoated glass slides. Furthermore, solvent contact times from 5 secondsto 10 minutes all yielded the same results for each of the solutionsapart from the 30% ethanol solution, for which a 5 second contact timeyielded slightly higher rates of germination than longer contact times.

A method for treating agricultural products so that they are sanitizedand preserved, and can, for example, be provided as Ready-to-Eat is nowdescribed. The treatment results in the agricultural products beingsufficiently sanitized, while also decreasing the mass loss rate andextending the shelf life of the produce in comparison to harvestedproduce that has not been treated. First, a solution is formed bydissolving a coating agent which includes a composition of monomers,oligomers, fatty acids, esters, amides, amines, thiols, carboxylicacids, ethers, aliphatic waxes, alcohols, salts (inorganic and organic),or combinations thereof (coating components) in a solvent, the solventincluding a sanitizing agent (e.g., ethanol, methanol, acetone,isopropanol, ethyl acetate, or combinations thereof). Specific examplesof compositions of the coating agent were described above and aredescribed in further detail below. The solution is then applied to thesurface of the agricultural product for a time sufficient for thesanitizing agent to sanitize the surface such that the product is safefor consumption without further washing. During the time that thesolution is applied to the agricultural product, the coating componentsform a protective coating over the surface. In some embodiments, theprotective coating prevents the sanitizing agent from damaging theagricultural product. In other embodiments, the protective coatingreplaces and/or reinforces portions of the natural coating covering theproduce (e.g., the cuticular layer) which are damaged by the sanitizingagent, thereby mitigating or eliminating the deleterious effects thesanitizing agent has on the surface. The composition of the coatingcomponents can be formulated such that the coating is edible andoptionally substantially undetectable. The solvent is then removed fromthe surface of the agricultural product, leaving the protective coatingon the surface. The coating, which remains on the surface of theagricultural product, serves as a barrier to biotic and/or abioticstressors such as moisture loss, oxidation, and fungal growth, therebymaintaining freshness and extending the shelf life of the agriculturalproduct even beyond that which is observed for similar products thathave not undergone washing, sanitization, or any other post-harvesttreatment. The method provides the advantage of treating the productusing a single process step that both sanitizes the product and alsocauses an extension in the shelf life of the product.

As previously described, the sanitizing agent can be any solvent whichis capable of sanitizing the surface of the produce. Examples includeethyl acetate, acetone, and alcohols such as ethanol, methanol, or,isopropanol, or combinations of any of the above. Historically, alcoholshave been some of the most commonly used substances for sanitizing anddisinfecting, and for example are used for disinfecting skin prior tohypodermic injections and finger pricks. Although the solvent can beformed entirely from the sanitizing agent, in many cases this has beenfound to lead to surface damage in produce even when a protective layeris formed. Diluting the sanitizing agent with water, such that thesolvent is about 90% sanitizing agent by volume or less, about 80%sanitizing agent by volume or less, or about 70% sanitizing agent byvolume or less has been found to substantially reduce surface damage fora variety of produce (for example, see FIGS. 13A-13B and 14A-14B).Furthermore, in some applications, many sanitizing agents have beenfound to more effectively sanitize surfaces when diluted with water. Forexample, ethanol and water mixtures which are in the range of about 50%to 80% ethanol have in some applications been found to be more effectivesanitizers than pure ethanol. Too weak of a dilution of the sanitizingagent (e.g., such that the sanitizing agent to water ratio is less thanabout 30/70, less than about 40/60, or less than about 50/50) canprevent the sanitizing agent from sufficiently sanitizing the surface ofthe agricultural product. Accordingly, in some embodiments, the solventincludes water and the sanitizing agent (e.g., ethanol) and is between40% and 95% sanitizing agent by volume, for example between 40% and 90%,between 40% and 80%, between 45% and 95%, between 45% and 90%, between45% and 80%, between 50% and 95%, between 50% and 90%, between 50% and80%, between 60% and 95%, between 60% and 90%, or between 60% and 80%sanitizing agent by volume. In particular embodiments, the sanitizingagent comprises ethanol, and the solvent includes ethanol and water andis between 40% and 95% ethanol by volume, for example between 50% and90%, between 50% and 80%, or between 60% and 80% ethanol by volume. Insome embodiments, the volume ratio of the sanitizing agent to water inthe solution is in a range of about 1 to 10.

The use of ethanol as a sanitizing or disinfecting agent has been widelyreported. For example, Morton reported on the bactericidal activity ofvarious concentrations of ethyl alcohol (ethanol) examined against avariety of microorganisms in exposure periods ranging from 10 seconds to1 hour. Pseudomonas aeruginosa. was killed in 10 seconds by allconcentrations of ethanol from 30% to 100% (v/v), and Serratiamarcescens, E, coli and Salmonella typhosa were killed in 10 seconds byall concentrations of ethanol from 40% to 100%. The gram-positiveorganisms Staphylococcus aureus and Streptococcus pyogenes were slightlymore resistant, being killed in 10 seconds by ethyl alcoholconcentrations of 60%-95% (Morton, Annals New York Academy of Sciences,53(1), 1950, pp. 191-196). Karabulut et al studied the effects ofpostharvest ethanol treatments of table grapes for controlling gray moldand found that ethanol concentrations of 30% or more applied for 10 atleast seconds inhibit the germination of Botrytis (Karabulut et al.,Postharvest Biology and Technology, 43 (2004) pp. 169-177). Oh et alstudied the antimicrobial activity of ethanol against Listeriamonocytogenes and found that 5% ethanol concentrations inhibit (but donot completely stop) growth of Listeria monocytogenes (Oh and Marshall,International Journal of Food Microbiology, 20 (1993) pp. 239-246).

As described above, the bacterial levels on the agricultural productfollowing the sanitization process depend at least partially on thespecific composition of the solvent and the duration of time that thesolution is applied to the product before the solvent is removed. Aminimum application time may be required in order to adequately sanitizethe products. Furthermore, a specific application time may also berequired in order to form a coating which adequately protects theagricultural product from damage and extends the shelf life of theproduct. It has been found that methods described herein for treatingproducts can effectively form coatings for application times in therange of about 5 seconds to 30 minutes, where shorter application timesare achieved by actively removing the solvent (e.g., by blowing air onthe treated products), while longer application times result when thesolvent is allowed to evaporate without any other form of activeremoval. In some cases, for example in large-scale treatment facilities,shorter application times may be preferable in order to increase thethroughput of the treated products.

Accordingly, in view of the above, the solution can be applied to thesurface of the agricultural product for between 1 and 3,600 seconds, forexample between 1 and 3000 seconds, between 1 and 2000 seconds, between1 and 1000 seconds, between 1 and 800 seconds, between 1 and 600seconds, between 1 and 500 seconds, between 1 and 400 seconds, between 1and 300 seconds, between 1 and 250 seconds, between 1 and 200 seconds,between 1 and 150 seconds, between 1 and 125 seconds, between 1 and 100seconds, between 1 and 80 seconds, between 1 and 60 seconds, between 1and 50 seconds, between 1 and 40 seconds, between 1 and 30 seconds,between 1 and 20 seconds, between 1 and 10 seconds, between 5 and 3000seconds, between 5 and 2000 seconds, between 5 and 1000 seconds, between5 and 800 seconds, between 5 and 600 seconds, between 5 and 500 seconds,between 5 and 400 seconds, between 5 and 300 seconds, between 5 and 250seconds, between 5 and 200 seconds, between 5 and 150 seconds, between 5and 125 seconds, between 5 and 100 seconds, between 5 and 80 seconds,between 5 and 60 seconds, between 5 and 50 seconds, between 5 and 40seconds, between 5 and 30 seconds, between 5 and 20 seconds, between 5and 10 seconds, between 10 and 3000 seconds, between 10 and 2000seconds, between 10 and 1000 seconds, between 10 and 800 seconds,between 10 and 600 seconds, between 10 and 500 seconds, between 10 and400 seconds, between 10 and 300 seconds, between 10 and 250 seconds,between 10 and 200 seconds, between 10 and 150 seconds, between 10 and125 seconds, between 10 and 100 seconds, between 10 and 80 seconds,between 10 and 60 seconds, between 10 and 50 seconds, between 10 and 40seconds, between 10 and 30 seconds, between 10 and 20 seconds, between20 and 100 seconds, between 100 and 3,000 seconds or between 500 and2,000 seconds. In some implementations, the sanitization process resultsin substantially reduced or substantially negligible bacteria, viral,and/or fungal levels on the surface of the agricultural product.

The protective coating formed from the coating agent can serve toprevent damage to the edible product (e.g., produce) caused by thesanitizing agent. The protective coating can increase the shelf life ofthe product. The protective coating formed from the coating agent canreplace or reinforce portions of the produce which are damaged by thesanitizing agent. The coating can form an edible coating over theproduce. In some embodiments, the product is a thin skin fruit orvegetable. For instance, the product can be a berry, grape, or apple. Insome embodiments, the product can include a cut fruit surface (e.g.,sliced apple). In some embodiments, the product includes a thick-skinnedfruit, optionally for which the skin has been removed to expose asurface of the underlying fruit, and optionally the fruit has been cut(e.g., avocado slices).

The specific composition of the coating agent can be formulated suchthat the resulting coating formed over the agricultural product mimicsor enhances the cuticular layer of the product. The biopolyester cutinforms the main structural component of the cuticle that composes theaerial surface of most land plants. Cutin is formed from a mixture ofpolymerized mono- and/or polyhydroxy fatty acids and embedded cuticularwaxes. The hydroxy fatty acids of the cuticle layer form tightly boundnetworks with high crosslink density, thereby acting as a barrier tomoisture loss and oxidation, as well as providing protection againstother environmental stressors.

The coating components (e.g., monomers, oligomers, fatty acids, esters,amides, amines, thiols, carboxylic acids, ethers, aliphatic waxes,alcohols, salts (inorganic and organic), or combinations thereof) whichare dissolved in the solvent can be extracted or derived from plantmatter, and in particular from cutin obtained from plant matter. Plantmatter typically includes some portions that contain cutin and/or have ahigh density of cutin (e.g., fruit peels, leaves, shoots, etc.), as wellas other portions that do not contain cutin or have a low density ofcutin (e.g., fruit flesh, seeds, etc.). The cutin-containing portionscan be formed from the monomer and/or oligomer units which aresubsequently utilized in the formulations described herein forpreparation of RTE agricultural products. The cutin-containing portionscan also include other constituents such as proteins, polysaccharides,phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids,alkaloids, alcohols, alkanes, and aldehydes, which may be included inthe coating agent or may be omitted.

The coating components (e.g., monomers, oligomers, fatty acids, esters,amides, amines, thiols, carboxylic acids, ethers, aliphatic waxes,alcohols, salts (inorganic and organic), or combinations thereof) can beobtained by first separating (or at least partially separating) portionsof the plant that include molecules desirable for formulations forforming protective barriers (e.g., RTE formulations) from those that donot include the desired molecules. For example, when utilizing cutin asthe feed stock for the solute composition, the cutin-containing portionsof the plant matter are separated (or at least partially separated) fromnon-cutin-containing portions, and cutin is obtained from thecutin-containing portions (e.g., when the cutin-containing portion is afruit peel, the cutin is separated from the peel). The obtained portionof the plant (e.g., cutin) is then depolymerized (or at least partiallydepolymerized) in order to obtain a mixture including a plurality offatty acid or esterified cutin monomers, oligomers, or combinationsthereof. The cutin derived monomers, oligomers, esters, or combinationsthereof can be directly dissolved in the solvent to form the formulationused in the preparation of the agricultural products (e.g., RTEproducts), or alternatively can first be activated or chemicallymodified (e.g., functionalized). Chemical modification or activationcan, for example, include glycerating the monomers, oligomers, orcombinations thereof to form a mixture of 1-monoacylglycerides and/or2-monoacylglycerides, and the mixture of 1-monoacylglycerides and/or2-monoacylglycerides is dissolved in the solvent to form a solution,thereby resulting in the formulation for preparation of the agriculturalproducts (e.g., RTE products).

In some implementations, the solute (e.g., the coating agent) of theformulation for preparation of agricultural products comprises fattyacids, esters, amides, amines, thiols, carboxylic acids, ethers,aliphatic waxes, alcohols, salts (inorganic and organic), orcombinations thereof. In some implementations, the solute comprisesmonoacylglyceride (e.g., 1-monoacylglyceride or 2-monoacylglyceride)esters of monomers and/or oligomers.

In some implementations, the solute (e.g., the coating agent) includescompounds of Formula I:

wherein:

-   -   R is selected from —H, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆        alkynyl, —C₃-C₇ cycloalkyl, aryl, or heteroaryl, wherein each        alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl is        optionally substituted with one or more C₁-C₆ alkyl or hydroxy;    -   R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹² and R¹³ are each        independently, at each occurrence, —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,        halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl, —C₃-C₇        cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl,        alkynyl, cycloalkyl, aryl, or heteroaryl is optionally        substituted with one or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, or halogen;    -   R³, R⁴, R⁷ and R⁸ are each independently, at each occurrence,        —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, halogen, —C₁-C₆ alkyl, —C₂-C₆        alkenyl, —C₂-C₆ alkynyl, —C₃-C₇ cycloalkyl, aryl, or heteroaryl,        wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or        heteroaryl is optionally substituted with —OR¹⁴, —NR¹⁴R¹⁵,        —SR¹⁴, or halogen; or    -   R³ and R⁴ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring heterocycle; and/or    -   R⁷ and R⁸ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring;    -   R¹⁴ and R¹⁵ are each independently, at each occurrence, —H,        —C₁-C₆ alkyl, —C₂-C₆ alkenyl, or —C₂-C₆ alkynyl;    -   the symbol        represents an optionally single or cis or trans double bond;    -   n is 0, 1, 2, 3, 4, 5, 6, 7, or 8;    -   m is 0, 1, 2, or 3;    -   q is 0, 1, 2, 3, 4, or 5; and    -   r is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

In some embodiments, R is —H, —CH₃, or —CH₂CH₃.

In some embodiments, the coating agent comprises monoacylglycerides(e.g., 1-monoacylglycerides or 2-monoacylglycerides). The differencebetween a 1-monoacylglyceride and a 2-monoacylglyceride is the point ofconnection of the glycerol ester. Accordingly, in some embodiments, thecoating agent comprises compounds of the Formula I-A (e.g.,2-monoacylglycerides):

wherein:

-   -   each R^(a) is independently —H or —C₁-C₆ alkyl;    -   each R^(b) is independently selected from —H, —C₁-C₆ alkyl, or        —OH;    -   R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹² and R¹³ are each        independently, at each occurrence, —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,        halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl, —C₃-C₇        cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl,        alkynyl, cycloalkyl, aryl, or heteroaryl is optionally        substituted with one or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, or halogen;    -   R³, R⁴, R⁷, and R⁸ are each independently, at each occurrence,        —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, halogen, —C₁-C₆ alkyl, —C₂-C₆        alkenyl, —C₂-C₆ alkynyl, —C₃-C₇ cycloalkyl, aryl, or heteroaryl        wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is        optionally substituted with one or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,        or halogen; or    -   R³ and R⁴ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring heterocycle; and/or    -   R⁷ and R⁸ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring heterocycle;    -   R¹⁴ and R¹⁵ are each independently, at each occurrence, —H,        —C₁-C₆ alkyl, —C₂-C₆ alkenyl, or —C₂-C₆ alkynyl;    -   the symbol        represents a single bond or a cis or trans double bond;    -   n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;    -   m is 0, 1, 2 or 3;    -   q is 0, 1, 2, 3, 4 or 5; and    -   r is 0, 1, 2, 3, 4, 5, 6, 7 or 8.

In some embodiments, the coating agent comprises compounds of theFormula I-B (e.g., 1-monoacylglycerides):

wherein:

-   -   each R^(a) is independently —H or —C₁-C₆ alkyl;    -   each R^(b) is independently selected from —H, —C₁-C₆ alkyl, or        —OH;    -   R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹² and R¹³ are each        independently, at each occurrence, —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,        halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl, —C₃-C₇        cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl,        alkynyl, cycloalkyl, aryl, or heteroaryl is optionally        substituted with one or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, or halogen;    -   R³, R⁴, R⁷, and R⁸ are each independently, at each occurrence,        —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, halogen, —C₁-C₆ alkyl, —C₂-C₆        alkenyl, —C₂-C₆ alkynyl, —C₃-C₇ cycloalkyl, aryl, or heteroaryl        wherein each alkyl, alkynyl, cycloalkyl, aryl, or heteroaryl is        optionally substituted with one or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,        or halogen; or    -   R³ and R⁴ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring heterocycle; and/or    -   R⁷ and R⁸ can combine with the carbon atoms to which they are        attached to form a C₃-C₆ cycloalkyl, a C₄-C₆ cycloalkenyl, or 3-        to 6-membered ring heterocycle;    -   R¹⁴ and R¹⁵ are each independently, at each occurrence, —H,        —C₁-C₆ alkyl, —C₂-C₆ alkenyl, or —C₂-C₆ alkynyl;    -   the symbol        represents a single bond or a cis or trans double bond;    -   n is 0, 1, 2, 3, 4, 5, 6, 7 or 8;    -   m is 0, 1, 2 or 3;    -   q is 0, 1, 2, 3, 4 or 5; and    -   r is 0, 1, 2, 3, 4, 5, 6, 7 or 8.

In some embodiments, the coating agent includes one or more of thefollowing fatty acid compounds:

In some embodiments, the coating agent includes one or more of thefollowing methyl ester compounds:

In some embodiments, the coating agent includes one or more of thefollowing ethyl ester compounds:

In some embodiments, the coating agent includes one or more of thefollowing 2-glycerol ester compounds:

In some embodiments, the coating agent includes one or more of thefollowing 1-glycerol ester compounds:

In some embodiments, the coating components (e.g., monomers, oligomers,fatty acids, esters, amides, amines, thiols, carboxylic acids, ethers,aliphatic waxes, alcohols, salts (inorganic and organic), orcombinations thereof) are derived from plant matter. In someembodiments, the coating components are derived from cutin. The steps ofsanitizing the produce and forming the protective coating over thesurface of the produce can result in the produce being Ready-to-Eat. Thesteps of sanitizing the produce and forming the protective coating overthe surface of the produce can also result in an increase in the shelflife of the produce as compared to untreated produce.

In some embodiments, the act of at least partially removing of thesolvent from the surface of the produce can comprise removing at least90% of the solvent from the surface of the produce.

Through extensive experimentation, the authors of the subject matterdisclosed herein have found that coatings formed from the above coatingcomponents, and in particular from various combinations of2-monoacylglycerides and one or more of the other compounds describedabove, are effective at preventing or mitigating surface damage causedby the sanitizing agent in a wide variety of agricultural products,including strawberries, blueberries, avocados, and finger limes.Furthermore, coatings formed from the above compounds have also beenshown to be highly effective in reducing water loss and increasing theshelf life of the agricultural products, making them well suited for RTEformulations.

Properties of the coating, such as thickness, cross-link density, andpermeability, can be varied to be suitable for a particular agriculturalproduct by adjusting the specific composition of the coating agent, thespecific composition of the solvent, the concentration of the coatingagent in the solvent, and the conditions of the sanitizationtreatment/coating deposition process. The concentration of the solute(e.g., coating agent) in the solvent can, for example, be in a range ofabout 0.5 mg/mL to 200 mg/mL. Techniques for applying the solution tothe surface of the agricultural product can, for example, includedipping and/or soaking the product in the solution or spraying thesolution onto the surface of the product.

FIG. 2 illustrates an example process 200 for preparing sanitized (e.g.,Ready-to-Eat or RTE) produce. First, a solid mixture of a coating agent(e.g., monomer and/or oligomer units) is dissolved in a solventincluding a sanitizing agent (e.g., ethanol or water/ethanol mixture) toform a solution (step 202). The concentration of the solid mixture inthe solvent can, for example, be in a range of about 0.1 to 200 mg/mL,such as in a range of about 0.1 to 100 mg/mL, 0.1 to 75 mg/mL, 0.1 to 50mg/mL, 0.1 to 30 mg/mL, 0.1 to 20 mg/mL, 0.5 to 200 mg/mL, 0.5 to 100mg/mL, 0.5 to 75 mg/mL, 0.5 to 50 mg/mL, 0.5 to 30 mg/mL, 0.5 to 20mg/mL, 1 to 200 mg/mL, 1 to 100 mg/mL, 1 to 75 mg/mL, 1 to 50 mg/mL, 1to 30 mg/mL, 1 to 20 mg/mL, 5 to 200 mg/mL, 5 to 100 mg/mL, 5 to 75mg/mL, 5 to 50 mg/mL, 5 to 30 mg/mL, or 5 to 20 mg/mL. Next, thesolution which includes the monomer and/or oligomer units is appliedover the surface of the produce to be coated (step 204), for example byspray coating the produce or by dipping the produce in the solution. Inthe case of spray coating, the solution can, for example, be placed in aspray bottle which generates a fine mist spray. The spray bottle headcan then be held approximately six to twelve inches from the produce,and the produce then sprayed. In the case of dip coating, the producecan, for example, be placed in a bag, the solution containing thecomposition poured into the bag, and the bag then sealed and lightlyagitated until the entire surface of the produce is wet. After applyingthe solution to the produce, the produce is allowed to dry until most orsubstantially all of the solvent has evaporated, thereby allowing acoating composed of the monomer and/or oligomer units to form over thesurface of the produce (step 206).

In some embodiments, the coating agent can independently be formulatedto sanitize the surface in addition to protecting the surface by forminga protective coating thereon. For example, the coating agent can includechemical components that incorporate into the coatings which areoperable to sanitize and/or disinfect the surface. In such embodiments,the subsequently formed coating may continue to reduce microorganismlevels on the surface even after the sanitizing agent has been removedfrom the surface. However, in some cases including sanitizing componentsin the coating agent can degrade the performance of the subsequentlyformed protective coating. As such, in many cases it can be preferablefor the sanitizing to be performed by the sanitizing agent (e.g., thesolvent) and for the coating agent to be free of or lacking anysanitizing components. That is, the coating agent can be anon-sanitizing coating agent.

Without wishing to be bound by theory, at least some of the coatingcompositions (e.g., compounds of Formula I) do not independently preventfungal growth or sanitize the surface of an edible substrate. Forexample, at least some coating compositions described herein, whenapplied to the surface of an edible substrate using water as a solvent,will not prevent fungal growth or sanitize the edible substrate.However, when the coating compositions described herein are dissolved ina solvent comprising a sanitizing agent, for example a solvent having atleast 30% ethanol (e.g., between 30% and 100% ethanol), the resultingsolutions can prevent fungal growth and/or sanitize the surface of theedible substrate. Additionally, the coating compositions left over onthe surface of the edible substrate can further serve to increase theshelf-life of the substrate (e.g., by preventing moisture loss).

EXAMPLES

The disclosure is further illustrated by the following examples andsynthesis examples, which are not to be construed as limiting thisdisclosure in scope or spirit to the specific procedures hereindescribed. It is to be understood that the examples are provided toillustrate certain embodiments and that no limitation to the scope ofthe disclosure is intended thereby. It is to be further understood thatresort may be had to various other embodiments, modifications, andequivalents thereof which may suggest themselves to those skilled in theart without departing from the spirit of the present disclosure and/orscope of the appended claims.

For each of the Examples below, palmitic acid was purchased from SigmaAldrich, 2,3-dihydroxypropan-1-yl hexadecanoate was purchased from TokyoChemical Industry Co, 1,3-dihydroxypropan-2-yl hexadecanoate wasprepared following the method of Example 1, stearic acid (octadecanoicacid) was purchased from Sigma Aldrich, 2,3-dihydroxypropan-1-yloctadecanoate was purchased from Alfa Aesar, 1,3-dihydroxypropan-2-yloctadecanoate was prepared following the method of Example 2,tetradecanoic acid was purchased from Sigma Aldrich,2,3-dihydroxypropan-1-yl tetradecanoate was purchased from TokyoChemical Industry Co, oleic acid was purchased from Sigma Aldrich, andethyl palmitate (EtPA) was purchased from Sigma Aldrich. All solventsand other chemical reagents were obtained from commercial sources (e.g.,Sigma-Aldrich (St. Louis, MO)) and were used without furtherpurification unless noted otherwise.

Example 1: Synthesis of 1,3-dihydroxypropan-2-yl Hexadecanoate for useas a Coating Agent Component

Step 1. 1,3-bis(benzyloxy)propan-2-yl hexadecanoate

70.62 g (275.34 mmol) of palmitic acid, 5.24 g (27.54 mmol) of p-TsOH,75 g (275.34 mmol) of 1,3-bis(benzyloxy)propan-2-ol, and 622 mL oftoluene were charged into a round bottom flask equipped with a Tefloncoated magnetic stir bar. A Dean-Stark Head and condenser were attachedto the flask and a positive flow of N₂ was initiated. The flask washeated to reflux in a heating mantle while the reaction mixture wasstirred vigorously until the amount of water collected (˜5 mL) in theDean-Stark Head indicated full ester conversion (˜8 hr). The flask wasallowed to cool down to room temperature and the reaction mixture waspoured into a separatory funnel containing 75 mL of a saturated aqueoussolution of Na₂CO₃ and 75 mL of brine. The toluene fraction wascollected and the aqueous layer was extracted with 125 mL of Et₂O. Theorganic layers were combined and washed with 100 mL of brine, dried overMgSO₄, filtered and concentrated in vacuo. The crude colorless oil wasdried under high vacuum providing (135.6 g, 265.49 mmol, crudeyield=96.4%) of 1,3-bis(benzyloxy)propan-2-yl hexadecanoate.

HRMS (ESI-TOF) (m/z): calcd. for C₃₃H₅₀O₄Na, [M+Na]⁺, 533.3607; found,533.3588;

¹H NMR (600 MHz, CDCl₃): δ 7.41-7.28 (m, 10H), 5.28 (p, J=5.0 Hz, 1H),4.59 (d, J=12.1 Hz, 2H), 4.54 (d, J=12.1 Hz, 2H), 3.68 (d, J=5.2 Hz,4H), 2.37 (t, J=7.5 Hz, 2H), 1.66 (p, J=7.4 Hz, 2H), 1.41-1.15 (m, 24H),0.92 (t, J=7.0 Hz, 3H) ppm.

¹³C NMR (151 MHz, CDCl₃): δ 173.37, 138.09, 128.43, 127.72, 127.66,73.31, 71.30, 68.81, 34.53, 32.03, 29.80, 29.79, 29.76, 29.72, 29.57,29.47, 29.40, 29.20, 25.10, 22.79, 14.23 ppm.

Step 2. 1,3-dihydroxypropan-2-yl hexadecanoate

7.66 g (15.00 mmol) of 1,3-bis(benzyloxy)propan-2-yl hexadecanoate, 79.8mg (0.75 mmol) of 10 wt % Pd/C and 100 mL of EtOAc were charged to a 3neck round bottom flask equipped with a Teflon coated magnetic stir bar.A cold finger, with a bubbler filled with oil attached to it, and abubbling stone connected to a 1:4 mixture of H₂/N₂ gas tank were affixedto the flask. H₂/N₂ was bubbled at 1.2 LPM into the flask until thedisappearance of both starting material and mono-deprotected substrateas determined by TLC (˜60 min). Once complete, the reaction mixture wasfiltered through a plug of Celite, which was then washed with 100 mL ofEtOAc. The filtrate was placed in a refrigerator at 4° C. for 24 hrs.The precipitate from the filtrate (white and transparent needles) wasfiltered and dried under high vacuum yielding (2.124 g, 6.427 mmol,yield=42.8%) of 1,3-dihydroxypropan-2-yl hexadecanoate.

HRMS (FD-TOF) (m/z): calcd. for C₁₉H₃₈O₄, 330.2770; found, 330.2757;

¹H NMR (600 MHz, CDCl₃): δ 4.93 (p, J=4.7 Hz, 1H), 3.84 (t, J=5.0 Hz,4H), 2.37 (t, J=7.6 Hz, 2H), 2.03 (t, J=6.0 Hz, 2H), 1.64 (p, J=7.6 Hz,2H), 1.38-1.17 (m, 26H), 0.88 (t, J=7.0 Hz, 3H) ppm.

¹³C NMR (151 MHz, CDCl₃): δ 174.22, 75.21, 62.73, 34.51, 32.08, 29.84,29.83, 29.81, 29.80, 29.75, 29.61, 29.51, 29.41, 29.26, 25.13, 22.85,14.27 ppm.

Example 2: Synthesis of 1,3-dihydroxypropan-2-yl Octadecanoate for useas a Coating Agent Component

Step 1. 1,3-bis(benzyloxy)propan-2-yl stearate

28.45 g (100 mmol) of stearic acid acid, 0.95 g (5 mmol) of p-TsOH,27.23 g (275.34 mmol) of 1,3-bis(benzyloxy)propan-2-ol, and 200 mL oftoluene were charged into a round bottom flask equipped with a Tefloncoated magnetic stir bar. A Dean-Stark Head and condenser were attachedto the flask and a positive flow of N2 was initiated. The flask washeated to reflux in an oil bath while the reaction mixture was stirredvigorously until the amount of water collected (˜1.8 mL) in theDean-Stark Head indicated full ester conversion (˜16 hr). The flask wasallowed to cool down to room temperature and the solution was dilutedwith 100 mL of hexanes. The reaction mixture was poured into aseparatory funnel containing 50 mL of a saturated aqueous solution ofNa₂CO₃. The organic fraction was collected and the aqueous layer wasextracted twice more with 50 mL portions of hexanes. The organic layerswere combined and washed with 100 mL of brine, dried over MgSO₄,filtered and concentrated in vacuo. The crude colorless oil was furtherpurified by selective liquid-liquid extraction using hexanes andacetonitrile and the product was again concentrated in vacuo, yielding(43.96 g, 81.60 mmol, yield=81.6%) of 1,3-bis(benzyloxy)propan-2-ylstearate.

¹H NMR (600 MHz, CDCl₃): δ 7.36-7.27 (m, 10H), 5.23 (p, J=5.0 Hz, 1H),4.55 (d, J=12.0 Hz, 2H), 4.51 (d, J=12.1 Hz, 2H), 3.65 (d, J=5.0 Hz,4H), 2.33 (t, J=7.5 Hz, 2H), 1.62 (p, J=7.4 Hz, 2H), 1.35-1.22 (m, 25H),0.88 (t, J=6.9 Hz, 3H) ppm.

Step 2. 1,3-dihydroxypropan-2-yl stearate

6.73 g (12.50 mmol) of 1,3-bis(benzyloxy)propan-2-yl stearate, 439 mg(0.625 mmol) of 20 wt % Pd(OH)₂/C and 125 mL of EtOAc were charged to a3 neck round bottom flask equipped with a Teflon coated magnetic stirbar. A cold finger, with a bubbler filled with oil attached to it, and abubbling stone connected to a 1:4 mixture of H₂/N₂ gas tank were affixedto the flask. H₂/N₂ was bubbled at 1.2 LPM into the flask until thedisappearance of both starting material and mono-deprotected substrateas determined by TLC (˜120 min). Once complete, the reaction mixture wasfiltered through a plug of Celite, which was then washed with 150 mL ofEtOAc. The filtrate was placed in a refrigerator at 4° C. for 48 hrs.The precipitate from the filtrate (white and transparent needles) wasfiltered and dried under high vacuum yielding (2.12 g, 5.91 mmol,yield=47.3%) of 1,3-dihydroxypropan-2-yl stearate.

LRMS (ESI+) (m/z): calcd. for C₂₁H₄₃O₄ [M+H]⁺, 359.32; found 359.47.

¹H NMR (600 MHz, CDCl₃): δ 4.92 (p, J=4.7 Hz, 1H), 3.88-3.78 (m, 4H),2.40-2.34 (m, 2H), 2.09 (t, J=6.2 Hz, 2H), 1.64 (p, J=7.3 Hz, 2H), 1.25(s, 25H), 0.88 (t, J=7.0 Hz, 3H) ppm.

¹³C NMR (151 MHz, CDCl₃): δ 174.32, 75.20, 62.63, 34.57, 32.14, 29.91,29.89, 29.87, 29.82, 29.68, 29.57, 29.47, 29.33, 25.17, 22.90, 14.32ppm.

Example 3: Effect of Ethanol on Post-Harvest Mass Loss of Blueberries

Blueberries were harvested simultaneously and divided into four groupsof sixty blueberries each, each of the groups being qualitativelyidentical (i.e., all groups had blueberries of approximately the sameaverage size and quality). The first group of blueberries was not washedor treated in any way and served as a control group. The second groupwas treated in a 1:1 mixture of ethanol and water. The third group wastreated in a 3:1 mixture of ethanol and water, and the fourth group wastreated in pure ethanol.

To treat the blueberries with the various solvents, the blueberries wereplaced in bags, and the solvent was poured into the bag. The bag wasthen sealed and lightly agitated until the entire surface of eachblueberry was wet. The blueberries were then removed from the bag andallowed to dry on drying racks. The blueberries were kept under ambientroom conditions at a temperature in the range of 23° C.-27° C. andhumidity in the range of 40%-55% while they dried and for the entireduration of the time they were tested.

FIG. 1 shows the percent mass loss of the four groups of blueberries asa function of time. Plot 102 shows the first (control) group. Plot 104shows the second group treated with 1:1 ethanol and water. Plot 106shows the third group treated with 3:1 ethanol and water. Plot 108 showsthe fourth group treated with pure ethanol.

Example 4: Use of Coating Agents to Reduce Spoilage ofBlueberries—Effect of Solvent

Two solutions of coating agents dissolved in a solvent were prepared toexamine the effect of the solvent on the rate of mass loss ofblueberries after treatment with the solution to form a coating over theblueberries. The first solution contained a 3:1 mixture by mass of1,3-dihydroxypropan-2-yl hexadecanoate (i.e., a 2-monoacylglyceride) and2,3-dihydroxypropan-1-yl hexadecanoate (i.e., a 1-monoacylglyceride)dissolved in pure ethanol at a concentration of 10 mg/mL. The secondsolution contained a 3:1 mixture by mass of 1,3-dihydroxypropan-2-ylhexadecanoate (i.e., a 2-monoacylglyceride) and 2,3-dihydroxypropan-1-ylhexadecanoate (i.e., a 1-monoacylglyceride) dissolved in a mixture of90% ethanol and 10% water at a concentration of 10 mg/mL.

Blueberries were harvested simultaneously and divided into three groupsof sixty blueberries each, each of the groups being qualitativelyidentical (i.e., all groups had blueberries of approximately the sameaverage size and quality). The first group of blueberries (correspondingto 302 in FIG. 3 ) was not washed or treated in any way and served as acontrol group. The second group was treated with the solution of1,3-dihydroxypropan-2-yl hexadecanoate and 2,3-dihydroxypropan-1-ylhexadecanoate (coating agent) in pure ethanol (sanitizing agent), andthe third group was treated with the solution of1,3-dihydroxypropan-2-yl hexadecanoate and 2,3-dihydroxypropan-1-ylhexadecanoate (coating agent) in the mixture of 90% ethanol (sanitizingagent) and 10% water.

Each of the treatments above, which served to sanitize the blueberriesand form the coatings, was performed as follows. The blueberries wereplaced in bags, and the solution containing the sanitizing agent and thecoating agent was poured into the bag. The bag was then sealed andlightly agitated until the entire surface of each blueberry was wet. Theblueberries were then removed from the bag and allowed to dry on dryingracks. The blueberries were kept under ambient room conditions at atemperature in the range of 23° C.-27° C. and humidity in the range of40%-55% while they dried and for the entire duration of the time theywere tested.

FIG. 3 shows plots of percent mass loss of blueberries versus time foruntreated (control) blueberries (plot 302), for blueberries treated withsolutions including coating agents dissolved in pure ethanol (plot 308),and for blueberries treated with coating agents dissolved in 90% ethanol(plot 306). As shown, the blueberries treated with solutions includingboth a sanitizing agent and a coating agent exhibited a substantiallylower rate of mass loss during the four days after harvesting ascompared to the untreated blueberries. After just under four days, theuntreated blueberries (302) experienced an average percent mass loss of15.4%, the blueberries treated in the solution including the coatingagent dissolved in pure ethanol (308) experienced an average percentmass loss of 11.8%, and the blueberries treated in the solutionincluding the coating agent dissolved in the 90% mixture of ethanol andwater (306) experienced an average percent mass loss of 10.6%.

Example 5: Use of Coating Agents to Reduce Spoilage ofBlueberries—Effect of Coating Agent Composition Using C₁₆ GlycerylEsters

Five solutions using C₁₆ glyceryl esters were prepared to examine theeffect of the coating agent composition on the rate of mass loss onblueberries treated with a solution comprising the coating agentdissolved in a sanitizing agent to form a coating over the blueberries.Each solution was composed of the coating agents described below in pureethanol at a concentration of 10 mg/mL. The first solution containedpure 2,3-dihydroxypropan-1-yl hexadecanoate. The second solutioncontained 75% 2,3-dihydroxypropan-1-yl hexadecanoate and 25%1,3-dihydroxypropan-2-yl hexadecanoate by mass. The third solutioncontained 50% 2,3-dihydroxypropan-1-yl hexadecanoate and 50%1,3-dihydroxypropan-2-yl hexadecanoate by mass. The fourth solutioncontained 25% 2,3-dihydroxypropan-1-yl hexadecanoate and 75%1,3-dihydroxypropan-2-yl hexadecanoate by mass. The fifth solutioncontained pure 1,3-dihydroxypropan-2-yl hexadecanoate.

Blueberries were harvested simultaneously and divided into six groups of60 blueberries each, each of the groups being qualitatively identical(i.e., all groups had blueberries of approximately the same average sizeand quality). In order to sanitize the blueberries and form thecoatings, the blueberries were placed in bags, and the solutioncontaining the sanitizing agent and the coating agent was poured intothe bag. The bag was then sealed and lightly agitated until the entiresurface of each blueberry was wet. The blueberries were then removedfrom the bag and allowed to dry on drying racks. The blueberries werekept under ambient room conditions at a temperature in the range of 23°C.-27° C. and humidity in the range of 40%-55% while they dried and forthe entire duration of the time they were tested.

FIG. 4 is a graph showing average daily mass loss rates for blueberriescoated with the five experimental coating solutions as well as a controlgroup of untreated blueberries, measured over the course of severaldays. As shown in FIG. 4 , the untreated blueberries (402) exhibited anaverage mass loss rate of 2.42% per day. The average daily mass lossrate of the blueberries treated with the pure 2,3-dihydroxypropan-1-ylhexadecanoate formulation (404) was 2.18%. The average daily mass lossrate of the blueberries treated with the pure 1,3-dihydroxypropan-2-ylhexadecanoate formulation (412) was 2.23%. The average daily mass lossrate of the blueberries treated with the formulation composed of 75%2,3-dihydroxypropan-1-yl hexadecanoate and 25% 1,3-dihydroxypropan-2-ylhexadecanoate (406) was 2.13%. The average daily mass loss rate of theblueberries treated with the formulation composed of 50%2,3-dihydroxypropan-1-yl hexadecanoate and 50% 1,3-dihydroxypropan-2-ylhexadecanoate (408) was 2.28%. The average daily mass loss rate of theblueberries treated with the formulation composed of 25%2,3-dihydroxypropan-1-yl hexadecanoate and 75% 1,3-dihydroxypropan-2-ylhexadecanoate (410) was 1.92%.

Example 6: Use of Coating Agents to Reduce Spoilage ofBlueberries—Effect of Coating Agent Composition Using C₁₈ GlycerylEsters

Five solutions using Cis glyceryl esters were prepared to examine theeffect of the coating agent composition on the rate of mass loss ofblueberries treated with a solution comprising the coating agentdissolved in a sanitizing agent to form a coating over the blueberries.Each solution was composed of the coating agents described below in pureethanol at a concentration of 10 mg/mL. The first solution containedpure 2,3-dihydroxypropan-1-yl octadecanoate. The second solutioncontained 75% 2,3-dihydroxypropan-1-yl octadecanoate and 25%1,3-dihydroxypropan-2-yl octadecanoate by mass. The third solutioncontained 50% 2,3-dihydroxypropan-1-yl octadecanoate and 50%1,3-dihydroxypropan-2-yl octadecanoate by mass. The fourth solutioncontained 25% 2,3-dihydroxypropan-1-yl octadecanoate and 75%1,3-dihydroxypropan-2-yl octadecanoate by mass. The fifth solutioncontained pure 1,3-dihydroxypropan-2-yl octadecanoate.

Blueberries were harvested simultaneously and divided into six groups of60 blueberries each, each of the groups being qualitatively identical(i.e., all groups had blueberries of approximately the same average sizeand quality). In order to sanitize the blueberries and form thecoatings, the blueberries were placed in bags, and the solutioncontaining the sanitizing agent and the coating agent was poured intothe bag. The bag was then sealed and lightly agitated until the entiresurface of each blueberry was wet. The blueberries were then removedfrom the bag and allowed to dry on drying racks. The blueberries werekept under ambient room conditions at a temperature in the range of 23°C.-27° C. and humidity in the range of 40%-55% while they dried and forthe entire duration of the time they were tested.

FIG. 5 is a graph showing average daily mass loss rates for blueberriescoated with the five experimental coating agents as well as a controlgroup of untreated blueberries, measured over the course of severaldays. As shown in FIG. 5 , the results for 2,3-dihydroxypropan-1-yloctadecanoate/1,3-dihydroxypropan-2-yl octadecanoate coating agentmixtures were similar to those for 2,3-dihydroxypropan-1-ylhexadecanoate/1,3-dihydroxypropan-2-yl hexadecanoate coating agentmixtures in FIG. 4 . The untreated blueberries (502) exhibited anaverage mass loss rate of 2.42% per day. The average daily mass lossrate of the blueberries treated with the pure 2,3-dihydroxypropan-1-yloctadecanoate formulation (504) was 2.11%. The average daily mass lossrate of the blueberries treated with the pure 1,3-dihydroxypropan-2-yloctadecanoate formulation (512) was 2.05%. The average daily mass lossrate of the blueberries treated with the formulation composed of 75%2,3-dihydroxypropan-1-yl octadecanoate and 25% 1,3-dihydroxypropan-2-yloctadecanoate (506) was 2.14%. The average daily mass loss rate of theblueberries treated with the formulation composed of 50%2,3-dihydroxypropan-1-yl octadecanoate and 50% 1,3-dihydroxypropan-2-yloctadecanoate (508) was 2.17%. The average daily mass loss rate of theblueberries treated with the formulation composed of 25%2,3-dihydroxypropan-1-yl octadecanoate and 75% 1,3-dihydroxypropan-2-yloctadecanoate (510) was 1.9%.

Example 7: Use of Coating Agents to Reduce Spoilage ofBlueberries—Effect of Coating Agent Concentration

Two solutions including a mixture of 2,3-dihydroxypropan-1-ylhexadecanoate (25%) and 1,3-dihydroxypropan-2-yl hexadecanoate (75%)(coating agent) dissolved in pure ethanol (sanitizing agent) wereprepared. For the first solution, the solute was dissolved in theethanol at a concentration of 10 mg/mL, and for the second solution, thesolute was dissolved in the ethanol at a concentration of 20 mg/mL.

Blueberries were harvested simultaneously and divided into three groupsof 60 blueberries each, each of the groups being qualitatively identical(i.e., all groups had blueberries of approximately the same average sizeand quality). The first group was a control group of untreatedblueberries, the second group was treated with the 10 mg/mL solution,and the third group was treated with the 20 mg/mL solution.

To treat the blueberries, each blueberry was picked up with a set oftweezers and individually dipped in the solution for approximately 1second, after which the blueberry was placed on a drying rack andallowed to dry. The blueberries were kept under ambient room conditionsat a temperature in the range of 23° C.-27° C. and humidity in the rangeof 40%-55% while they dried and for the entire duration of the time theywere tested. Mass loss was measured by carefully weighing theblueberries each day, where the reported percent mass loss was equal tothe ratio of mass reduction to initial mass.

FIG. 6 shows plots of the percent mass loss over the course of 5 days inuntreated (control) blueberries (602), blueberries treated using thefirst solution of 10 mg/mL (604), and blueberries treated using thesecond solution of 20 mg/mL. As shown, the percent mass loss foruntreated blueberries was 19.2% after 5 days, whereas the percent massloss for blueberries treated with the 10 mg/mL solution was 15% after 5days, and the percent mass loss for blueberries treated with the 20mg/mL solution was 10% after 5 days.

FIG. 7 shows high resolution photographs of the untreated blueberries(602) and of the blueberries treated with the 10 mg/mL solution, takenat day 5. The skins of the uncoated blueberries (602) were highlywrinkled as a result of mass loss of the blueberries, whereas the skinsof the blueberries treated with the 10 mg/mL solution (604) remainedvery smooth.

Example 8: Use of Coating Agents to Reduce Spoilage ofStrawberries—Effect of Coating Agent Composition Using C₁₆ GlycerylEsters

Five solutions using C₁₆ glyceryl esters were prepared to examine theeffect of the coating agent composition on the rate of mass loss onstrawberries treated with a solution comprising the coating agentdissolved in a sanitizing agent to form a coating over the strawberries.Each solution was composed of the coating agents described below in pureethanol at a concentration of 10 mg/mL.

The first solution contained pure 2,3-dihydroxypropan-1-ylhexadecanoate. The second solution contained 75%2,3-dihydroxypropan-1-yl hexadecanoate and 25% 1,3-dihydroxypropan-2-ylhexadecanoate by mass. The third solution contained 50%2,3-dihydroxypropan-1-yl hexadecanoate and 50% 1,3-dihydroxypropan-2-ylhexadecanoate by mass. The fourth solution contained 25%2,3-dihydroxypropan-1-yl hexadecanoate and 75% 1,3-dihydroxypropan-2-ylhexadecanoate by mass. The fifth solution contained pure1,3-dihydroxypropan-2-yl hexadecanoate.

Strawberries were harvested simultaneously and divided into six groupsof 15 strawberries each, each of the groups being qualitativelyidentical (i.e., all groups had strawberries of approximately the sameaverage size and quality). In order to sanitize the strawberries andform the coatings, the strawberries were spray coated according to thefollowing procedure. First, the strawberries were placed on dryingracks. The five solutions were each placed in a spray bottle whichgenerated a fine mist spray. For each bottle, the spray head was heldapproximately six inches from the strawberries, and the strawberrieswere sprayed and then allowed to dry on the drying racks. Thestrawberries were kept under ambient room conditions at a temperature inthe range of 23° C.-27° C. and humidity in the range of 40%-55% whilethey dried and for the entire duration of the time they were tested.

FIG. 8 is a graph showing average daily mass loss rates, measured overthe course of 4 days, of the strawberries treated with each of the fivesolutions described above. The strawberries corresponding to bar 802were untreated (control group). The strawberries corresponding to bar804 were treated with the first solution (i.e., pure2,3-dihydroxypropan-1-yl hexadecanoate). The strawberries correspondingto bar 806 were treated with the second solution (i.e., 75%2,3-dihydroxypropan-1-yl hexadecanoate and 25% 1,3-dihydroxypropan-2-ylhexadecanoate). The strawberries corresponding to bar 808 were treatedwith the third solution (i.e., 50% 2,3-dihydroxypropan-1-ylhexadecanoate and 50% 1,3-dihydroxypropan-2-yl hexadecanoate). Thestrawberries corresponding to bar 810 were treated with the fourthsolution (i.e., 25% 2,3-dihydroxypropan-1-yl hexadecanoate and 75%1,3-dihydroxypropan-2-yl hexadecanoate). The strawberries correspondingto bar 812 were treated with the fifth solution (i.e., pure1,3-dihydroxypropan-2-yl hexadecanoate).

As shown in FIG. 8 , the untreated strawberries (802) exhibited anaverage mass loss rate of 7.6% per day. The strawberries treated withthe pure 2,3-dihydroxypropan-1-yl hexadecanoate formulation (804)exhibited an average daily mass loss rate of 6.4%. The strawberriestreated with the pure 1,3-dihydroxypropan-2-yl hexadecanoate formulation(812) exhibited an average daily mass loss rate of 6.1%. Thestrawberries corresponding to bar 806 (2,3-dihydroxypropan-1-ylhexadecanoate to 1,3-dihydroxypropan-2-yl hexadecanoate mass ratio of 3)exhibited an average daily mass loss rate of 5.9%. The strawberriescorresponding to bar 808 exhibited an average daily mass loss rate of5.1%. The strawberries corresponding to bar 810 exhibited an averagedaily mass loss rate of 4.8%.

FIG. 9 shows high resolution photographs of 4 coated and 4 uncoatedstrawberries over the course of 5 days at the temperature and humidityconditions described above, where the coated strawberries were treatedwith a solution for which the coating agent was a mixture of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate combined at a mass ratio of 0.33, as in bar 810 in FIG. 8. As seen, the untreated strawberries began to exhibit fungal growth anddiscoloration by day 3, and were mostly covered in fungus by day 5. Incontrast, the treated strawberries did not exhibit any fungal growth byday 5 and were largely similar in overall color and appearance on day 1and day 5.

Example 9: Use of Coating Agents to Reduce Spoilage of Avocados—Effectof Coating Agent Composition Using Combinations of 1-Glyceryl and2-Glyceryl Esters

Nine solutions using combinations 1-glyceryl and 2-glyceryl esters wereprepared to examine the effect of the coating agent composition on therate of mass loss on avocados treated with a solution comprising thecoating agent dissolved in a sanitizing agent to form a coating over theavocados. Each solution was composed of the coating agents describedbelow dissolved in pure ethanol (sanitizing agent) at a concentration of5 mg/mL.

The first solution contained 2,3-dihydroxypropan-1-yl tetradecanoate and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:3.The second solution contained 2,3-dihydroxypropan-1-yl tetradecanoateand 1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of1:1. The third solution contained 2,3-dihydroxypropan-1-yltetradecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate combined at amolar ratio of 3:1. The fourth solution contained2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate combined at a molar ratio of 3:1. The fifth solutioncontained 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:1.The sixth solution contained 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:3.The seventh solution contained 2,3-dihydroxypropan-1-yl octadecanoateand 1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of1:3. The eighth solution contained 2,3-dihydroxypropan-1-yloctadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate combined at amolar ratio of 1:1. The ninth solution contained2,3-dihydroxypropan-1-yl octadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate combined at a molar ratio of 3:1.

Avocados were harvested simultaneously and divided into nine groups of30 avocados, each of the groups being qualitatively identical (i.e., allgroups had avocados of approximately the same average size and quality).In order to sanitize the avocados and form the coatings, the avocadoswere each individually dipped in one of the solutions, with each groupof 30 avocados being treated with the same solution. The avocados werethen placed on drying racks and allowed to dry under ambient roomconditions at a temperature in the range of about 23° C.-27° C. andrelative humidity in the range of about 40%-55%. The avocados were allheld at these same temperature and humidity conditions for the entireduration of time they were tested.

FIG. 10 is a graph showing the shelf life factor for avocados that wereeach treated with one of the nine solutions described above. Bar 1002corresponds to the first solution (1:3 mixture of2,3-dihydroxypropan-1-yl tetradecanoate (MA1G) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1004 corresponds tothe second solution (1:1 mixture of 2,3-dihydroxypropan-1-yltetradecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate), bar 1006corresponds to the third solution (3:1 mixture of2,3-dihydroxypropan-1-yl tetradecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate), bar 1012 corresponds to the fourth solution (1:3 mixtureof 2,3-dihydroxypropan-1-yl hexadecanoate (PA1G) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1014 corresponds tothe fifth solution (1:1 mixture of 2,3-dihydroxypropan-1-ylhexadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate), bar 1016corresponds to the sixth solution (3:1 mixture of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate), bar 1022 corresponds to the seventh solution (1:3mixture of 2,3-dihydroxypropan-1-yl octadecanoate (SA1G) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1024 corresponds tothe eighth solution (1:1 mixture of 2,3-dihydroxypropan-1-yloctadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate), and bar 1026corresponds to the ninth solution (3:1 mixture of2,3-dihydroxypropan-1-yl octadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate). As used herein, the term “shelf life factor” is definedas the ratio of the average daily mass loss rate of untreated produce(measured for a control group) to the average daily mass loss rate ofthe corresponding treated produce. Hence, a shelf life factor greaterthan 1 corresponds to a decrease in average daily mass loss rate oftreated produce as compared to untreated produce, and a larger shelflife factor corresponds to a greater reduction in average daily massloss rate.

As shown in FIG. 10 , treatment in the first solution (1002) resulted ina shelf life factor of 1.48, treatment in the second solution (1004)resulted in a shelf life factor of 1.42, treatment in the third solution(1006) resulted in a shelf life factor of 1.35, treatment in the fourthsolution (1012) resulted in a shelf life factor of 1.53, treatment inthe fifth solution (1014) resulted in a shelf life factor of 1.45,treatment in the sixth solution (1016) resulted in a shelf life factorof 1.58, treatment in the seventh solution (1022) resulted in a shelflife factor of 1.54, treatment in the eighth solution (1024) resulted ina shelf life factor of 1.47, and treatment in the ninth solution (1026)resulted in a shelf life factor of 1.52.

Example 10: Use of Coating Agents to Reduce Spoilage of Avocados—Effectof Coating Agent Composition Using Combinations of Fatty Acids andGlyceryl Esters

Nine solutions using combinations fatty acids and glyceryl esters wereprepared to examine the effect of the coating agent composition on therate of mass loss on avocados treated with a solution comprising thecoating agent dissolved in a sanitizing agent to form a coating over theavocados. Each solution was composed of the coating agents describedbelow dissolved in pure ethanol (sanitizing agent) at a concentration of5 mg/mL.

The first solution contained tetradecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:3.The second solution contained tetradecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:1.The third solution contained tetradecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 3:1.The fourth solution contained hexadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:3.The fifth solution contained hexadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:1.The sixth solution contained hexadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 3:1.The seventh solution contained octadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:3.The eighth solution contained octadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:1.The ninth solution contained octadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 3:1.

Avocados were harvested simultaneously and divided into nine groups of30 avocados, each of the groups being qualitatively identical (i.e., allgroups had avocados of approximately the same average size and quality).In order to sanitize the avocados and form the coatings, the avocadoswere each individually dipped in one of the solutions, with each groupof 30 avocados being treated with the same solution. The avocados werethen placed on drying racks and allowed to dry under ambient roomconditions at a temperature in the range of about 23° C.-27° C. andrelative humidity in the range of about 40%-55%. The avocados were allheld at these same temperature and humidity conditions for the entireduration of time they were tested.

FIG. 11 is a graph showing the shelf life factor for avocados that wereeach treated with one of the nine solutions described above. Bar 1102corresponds to the first solution (1:3 mixture of tetradecanoic acid(MA) and 1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1104corresponds to the second solution (1:1 mixture of tetradecanoic acidand 1,3-dihydroxypropan-2-yl hexadecanoate), bar 1106 corresponds to thethird solution (3:1 mixture of tetradecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate), bar 1112 corresponds to thefourth solution (1:3 mixture of hexadecanoic acid (PA) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1114 corresponds tothe fifth solution (1:1 mixture of hexadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate), bar 1116 corresponds to thesixth solution (3:1 mixture of hexadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate), bar 1122 corresponds to theseventh solution (1:3 mixture of octadecanoic acid (SA)_and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1124 corresponds tothe eighth solution (1:1 mixture of octadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate), and bar 1126 corresponds to theninth solution (3:1 mixture of octadecanoic acid and1,3-dihydroxypropan-2-yl hexadecanoate).

As shown in FIG. 11 , treatment in the first solution (1102) resulted ina shelf life factor of 1.39, treatment in the second solution (1104)resulted in a shelf life factor of 1.35, treatment in the third solution(1106) resulted in a shelf life factor of 1.26, treatment in the fourthsolution (1112) resulted in a shelf life factor of 1.48, treatment inthe fifth solution (1114) resulted in a shelf life factor of 1.40,treatment in the sixth solution (1116) resulted in a shelf life factorof 1.30, treatment in the seventh solution (1122) resulted in a shelflife factor of 1.54, treatment in the eighth solution (1124) resulted ina shelf life factor of 1.45, and treatment in the ninth solution (1126)resulted in a shelf life factor of 1.35.

Example 11: Use of Coating Agents to Reduce Spoilage of Avocados—Effectof Coating Agent Composition Using Combinations of Ethyl Esters andGlyceryl Esters or Fatty Acids and Glyceryl Esters

Fifteen solutions using combinations ethyl esters and glyceryl esters orfatty acids and glyceryl esters were prepared to examine the effect ofthe coating agent composition on the rate of mass loss on avocadostreated with a solution comprising the coating agent dissolved in asanitizing agent to form a coating over the avocados. Each solution wascomposed of the coating agents described below dissolved in pure ethanol(sanitizing agent) at a concentration of 5 mg/mL.

The first solution contained ethyl palmitate and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:3.The second solution contained ethyl palmitate and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 1:1.The third solution contained ethyl palmitate and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 3:1.The fourth solution contained oleic acid and 1,3-dihydroxypropan-2-ylhexadecanoate combined at a molar ratio of 1:3. The fifth solutioncontained oleic acid and 1,3-dihydroxypropan-2-yl hexadecanoate combinedat a molar ratio of 1:1. The sixth solution contained oleic acid and1,3-dihydroxypropan-2-yl hexadecanoate combined at a molar ratio of 3:1.The seventh solution contained tetradecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 1:3.The eighth solution contained tetradecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 1:1.The ninth solution contained tetradecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 3:1.The tenth solution contained hexadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 1:3.The eleventh solution contained hexadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 1:1.The twelfth solution contained hexadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 3:1.The thirteenth solution contained octadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 1:3.The fourteenth solution contained octadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 1:1.The fifteenth solution contained octadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate combined at a molar ratio of 3:1.

Avocados were harvested simultaneously and divided into fifteen groupsof 30 avocados, each of the groups being qualitatively identical (i.e.,all groups had avocados of approximately the same average size andquality). In order to sanitize the avocados and form the coatings, theavocados were each individually dipped in one of the solutions, witheach group of 30 avocados being treated with the same solution. Theavocados were then placed on drying racks and allowed to dry underambient room conditions at a temperature in the range of about 23°C.-27° C. and relative humidity in the range of about 40%-55%. Theavocados were all held at these same temperature and humidity conditionsfor the entire duration of time they were tested.

FIG. 12 is a graph showing the shelf life factor for avocados that wereeach treated with one of the fifteen solutions described above. Bar 1201corresponds to the first solution (1:3 mixture of ethyl palmitate (EtPA)and 1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1202 correspondsto the second solution (1:1 mixture of ethyl palmitate and1,3-dihydroxypropan-2-yl hexadecanoate), bar 1203 corresponds to thethird solution (3:1 mixture of ethyl palmitate and1,3-dihydroxypropan-2-yl hexadecanoate), bar 1211 corresponds to thefourth solution (1:3 mixture of oleic acid (OA) and1,3-dihydroxypropan-2-yl hexadecanoate (PA2G)), bar 1212 corresponds tothe fifth solution (1:1 mixture of oleic acid and1,3-dihydroxypropan-2-yl hexadecanoate), bar 1213 corresponds to thesixth solution (3:1 mixture of oleic acid and 1,3-dihydroxypropan-2-ylhexadecanoate), bar 1221 corresponds to the seventh solution (1:3mixture of tetradecanoic acid (MA) and 2,3-dihydroxypropan-1-yloctadecanoate (SA1G)), bar 1222 corresponds to the eighth solution (1:1mixture of tetradecanoic acid and 2,3-dihydroxypropan-1-yloctadecanoate), bar 1223 corresponds to the ninth solution (3:1 mixtureof octadecanoic acid and 2,3-dihydroxypropan-1-yl tetradecanoic), bar1231 corresponds to the tenth solution (1:3 mixture of hexadecanoic acid(PA) and 2,3-dihydroxypropan-1-yl octadecanoate (SA1G)), bar 1232corresponds to the eleventh solution (1:1 mixture of hexadecanoic acidand 2,3-dihydroxypropan-1-yl octadecanoate), bar 1233 corresponds to thetwelfth solution (3:1 mixture of hexadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate), bar 1241 corresponds to thethirteenth solution (1:3 mixture of octadecanoic acid (SA) and2,3-dihydroxypropan-1-yl octadecanoate (SA1G)), bar 1242 corresponds tothe fourteenth solution (1:1 mixture of octadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate), and bar 1243 corresponds to thefifteenth solution (3:1 mixture of octadecanoic acid and2,3-dihydroxypropan-1-yl octadecanoate).

As shown in FIG. 12 , treatment in the first solution (1201) resulted ina shelf life factor of 1.54, treatment in the second solution (1202)resulted in a shelf life factor of 1.45, treatment in the third solution(1203) resulted in a shelf life factor of 1.32, treatment in the fourthsolution (1211) resulted in a shelf life factor of 1.50, treatment inthe fifth solution (1212) resulted in a shelf life factor of 1.32,treatment in the sixth solution (1213) resulted in a shelf life factorof 1.29, treatment in the seventh solution (1221) resulted in a shelflife factor of 1.76, treatment in the eighth solution (1222) resulted ina shelf life factor of 1.68, treatment in the ninth solution (1223)resulted in a shelf life factor of 1.46, treatment in the tenth solution(1231) resulted in a shelf life factor of 1.72, treatment in theeleventh solution (1232) resulted in a shelf life factor of 1.66,treatment in the twelfth solution (1233) resulted in a shelf life factorof 1.56, treatment in the thirteenth solution (1241) resulted in a shelflife factor of 1.76, treatment in the fourteenth solution (1242)resulted in a shelf life factor of 1.70, and treatment in the fifteenthsolution (1243) resulted in a shelf life factor of 1.47.

Example 12: Effect of Solvent Composition in Solutions Used to TreatPomegranates

Two solutions of coating agents dissolved in a solvent were prepared toexamine the effect of the solvent composition on skin damage inpomegranates after treatment with the solution to form a coating overthe pomegranates. The first solution contained a 30:70 mixture by massof 2,3-dihydroxypropan-1-yl hexadecanoate (i.e., a 1-monoacylglyceride)and 1,3-dihydroxypropan-2-yl hexadecanoate (i.e., a 2-monoacylglyceride)dissolved in pure ethanol at a concentration of 40 mg/mL. The secondsolution contained a 30:70 mixture by mass of 2,3-dihydroxypropan-1-ylhexadecanoate (i.e., a 1-monoacylglyceride) and 1,3-dihydroxypropan-2-ylhexadecanoate (i.e., a 2-monoacylglyceride) dissolved in a mixture of70% ethanol and 30% water at a concentration of 40 mg/mL.

Pomegranates were harvested simultaneously and divided into two groupsof ten pomegranates each, with each of the groups being qualitativelyidentical (i.e., all groups had pomegranates of approximately the sameaverage size and quality). The first group of pomegranates(corresponding to FIG. 13A) was treated with the solution of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate (coating agent) in pure ethanol (sanitizing agent), andthe second group (corresponding to FIG. 13B) was treated with thesolution of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate (coating agent) in the mixture of70% ethanol (sanitizing agent) and 30% water.

Each of the treatments above, which served to sanitize the pomegranatesand form coatings, was performed as follows. The pomegranates wereplaced in bags, and the solution containing the sanitizing agent and thecoating agent was poured into the bag. The bag was then sealed andlightly agitated until the entire surface of each pomegranate was wet.The pomegranates were then removed from the bag and allowed to dry ondrying racks. The pomegranates were kept under ambient room conditionsat a temperature in the range of 23° C.-27° C. and humidity in the rangeof 40%-55% while they dried and for the entire duration of the time theywere tested.

FIG. 13A is a high resolution photograph of one of the pomegranates thatwas treated with the first solution (30:70 mixture of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate dissolved in pure ethanol), and FIG. 13B is a highresolution photograph of one of the pomegranates that was treated withthe second solution (30:70 mixture of 2,3-dihydroxypropan-1-ylhexadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate dissolved in70% ethanol). For the pomegranates treated with the 100% ethanolsolution (FIG. 13A), the solvent contacted the surfaces of thepomegranates for about 30-60 seconds on average before completelyevaporating away, after which the coating agent remained on thesurfaces. For the pomegranates treated with the 70% ethanol solution(FIG. 13B), the solvent contacted the surfaces of the pomegranates forabout 10 minutes on average before completely evaporating away, afterwhich the coating agent remained on the surfaces. The images in FIGS.13A and 13B are similar to and representative of all the otherpomegranates in the respective groups. Visible skin breakdown wasobserved in all the pomegranates treated with the 100% ethanol solution(FIG. 13A), whereas the pomegranates treated with the 70% ethanolsolution (FIG. 13B) all appeared undamaged and were otherwise unalteredin appearance by the treatment.

Example 13: Effect of Solvent Composition in Solutions Used to TreatLimes

Two solutions of coating agents dissolved in a solvent were prepared toexamine the effect of the solvent composition on skin damage in limesafter treatment with the solution to form a coating over the limes. Thefirst solution contained a 30:70 mixture by mass of2,3-dihydroxypropan-1-yl hexadecanoate (i.e., a 1-monoacylglyceride) and1,3-dihydroxypropan-2-yl hexadecanoate (i.e., a 2-monoacylglyceride)dissolved in pure ethanol at a concentration of 40 mg/mL. The secondsolution contained a 30:70 mixture by mass of 2,3-dihydroxypropan-1-ylhexadecanoate (i.e., a 1-monoacylglyceride) and 1,3-dihydroxypropan-2-ylhexadecanoate (i.e., a 2-monoacylglyceride) dissolved in a mixture of80% ethanol and 20% water at a concentration of 40 mg/mL.

Limes were harvested simultaneously and divided into two groups of sixlimes each, each of the groups being qualitatively identical (i.e., allgroups had limes of approximately the same average size and quality).The first group of limes (corresponding to FIG. 14A) was treated withthe solution of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate (coating agent) in pure ethanol(sanitizing agent), and the second group (corresponding to FIG. 14B) wastreated with the solution of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate (coating agent) in the mixture of80% ethanol (sanitizing agent) and 20% water.

Each of the treatments above, which served to sanitize the limes andform coatings, was performed as follows. The limes were placed in bags,and the solution containing the sanitizing agent and the coating agentwas poured into the bag. The bag was then sealed and lightly agitateduntil the entire surface of each lime was wet. The limes were thenremoved from the bag and allowed to dry on drying racks. The limes werekept under ambient room conditions at a temperature in the range of 23°C.-27° C. and humidity in the range of 40%-55% while they dried and forthe entire duration of the time they were tested.

FIG. 14A is a high resolution photograph of one of the limes that wastreated with the first solution (30:70 mixture of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate dissolved in pure ethanol), and FIG. 14B is a highresolution photograph of one of the limes that was treated with thesecond solution (30:70 mixture of 2,3-dihydroxypropan-1-yl hexadecanoateand 1,3-dihydroxypropan-2-yl hexadecanoate dissolved in 80% ethanol).For the limes treated with the 100% ethanol solution (FIG. 14A), thesolvent contacted the surfaces of the limes for about 30-60 secondsbefore completely evaporating away, after which the coating agentremained on the surfaces. For the limes treated with the 80% ethanolsolution (FIG. 14B), the solvent contacted the surfaces of the limes forabout 10 minutes before completely evaporating away, after which thecoating agent remained on the surfaces. The images in FIGS. 14A and 14Bare similar to and representative of all the other limes in therespective groups. Visible skin breakdown was observed in all the limestreated with the 100% ethanol solution (FIG. 14A), whereas the limestreated with the 80% ethanol solution (FIG. 14B) all appeared undamagedand were otherwise unaltered in appearance by the treatment.

Example 14: Spores Germinate on Top of Coating Compositions

2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate (i.e., a coating composition) were combined in a 30:70ratio and dissolved in 100% ethanol at a concentration of 10 mg/mL toform a solution. 10 μL of the solution was deposited onto glass slidescoated with fruit wax. The solvent (ethanol) was allowed to evaporate,leaving a residue of coating composition. 20 μL droplets of spores ofeither Colletotrichum or Botrytis spp. suspended in sterile water at aconcentration of ˜104 spores/mL were deposited on top of the coatedslides. The samples were incubated for 24 hours at 20° C. atapproximately 90% relative humidity, stained with lactophenol blue dye(diluted to 20% strength in sterile water), and imaged using a lightmicroscope. Five samples per condition (i.e., Colletotrichum andBotrytis spp) were studied.

FIG. 15A shows a microscope image 1500 of a coated slide afteradministration of Colletotrichum spores 1502. The image isrepresentative of all five samples examined. It was found that over 95%of Colletotrichum spores germinated on top of the coating composition.

FIG. 15B shows a microscope image 1510 of a coated slide afteradministration of Botrytis spores 1512. The image is representative ofall five samples examined. It was found that over 95% of Botrytis sporesgerminated on top of the coating composition.

Example 15: Ethanol/Water Mixtures Composed of 30% or Greater EthanolInhibit Germination and Growth of Spores

20 μL droplets of spores of either Colletotrichum or Botrytis spp.suspended in sterile water at a concentration of ˜10⁴ spores/mL weredeposited on top of microscope slides coated with fruit wax. The sporeswere allowed to settle for 30 minutes and the water droplet wasaspirated off with a Kimwipe.

On top of the spore-treated slides was deposited 10 μL of a solution of0%, 10%, 30%, 50%, 70%, 90%, or 100% ethanol in deionized, sterilewater; or 10 μL of 70%, 90% or 100% ethanol solutions containing 10mg/mL of 2,3-dihydroxypropan-1-yl hexadecanoate and1,3-dihydroxypropan-2-yl hexadecanoate at a ratio of 30:70. After 10minutes, any remaining solvent was aspirated off with a Kimwipe and a 20μL droplet of sterile, deionized water was deposited onto each sample.The samples were incubated for 24 hours at 20° C. at approximately 90%relative humidity, stained with lactophenol blue dye (diluted to 20%strength in sterile water), and imaged on a light microscope. For eachspore species and each experimental condition, five samples werestudied.

FIGS. 16A-16G and 17A-17C show representative microscope images (1600,1610, 1620, 1630, 1640, 1650, 1660, 1740, 1750, and 1760, respectively)of Colletotrichum-coated slides after treatment with the compositionsdescribed above. FIG. 16A corresponds to treatment with water (0%ethanol). FIG. 16B corresponds to treatment with a 10% ethanol solution.FIG. 16C corresponds to treatment with a 30% ethanol solution. FIG. 16Dcorresponds to treatment with a 50% ethanol solution. FIG. 16Ecorresponds to treatment with a 70% ethanol solution. FIG. 16Fcorresponds to treatment with a 90% ethanol solution. FIG. 16Gcorresponds to treatment with pure ethanol. FIG. 17A corresponds totreatment with a 70% ethanol solution containing 10 mg/mL of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate at a ratio of 30:70. FIG. 17B corresponds to treatmentwith a 90% ethanol solution containing 10 mg/mL of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate at a ratio of 30:70. FIG. 17C corresponds to treatmentwith pure ethanol containing 10 mg/mL of 2,3-dihydroxypropan-1-ylhexadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate at a ratio of30:70. Each image is representative of the other four samples examined.Spores in the various images are numbered 1602, 1612, 1622, 1632, 1642,1652, 1662, 1742, 1752, and 1762. For the sake of clarity, only onespore is labeled per image.

FIGS. 18A-18G and 19A-19C show representative microscope images (1800,1810, 1820, 1830, 1840, 1850, 1860, 1890, 1950, and 1960, respectively)of Botrytis-coated slides after treatment with the compositionsdescribed above. FIG. 18A corresponds to treatment with water (0%ethanol). FIG. 18B corresponds to treatment with a 10% ethanol solution.FIG. 18C corresponds to treatment with a 30% ethanol solution. FIG. 18Dcorresponds to treatment with a 50% ethanol solution. FIG. 18Ecorresponds to treatment with a 70% ethanol solution. FIG. 18Fcorresponds to treatment with a 90% ethanol solution. FIG. 18Gcorresponds to treatment with pure ethanol. FIG. 19A corresponds totreatment with a 70% ethanol solution containing mg/mL of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate at a ratio of 30:70. FIG. 19B corresponds to treatmentwith a 90% ethanol solution containing 10 mg/mL of2,3-dihydroxypropan-1-yl hexadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate at a ratio of 30:70. FIG. 19C corresponds to treatmentwith pure ethanol containing 10 mg/mL of 2,3-dihydroxypropan-1-ylhexadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate at a ratio of30:70. Each image is representative of the other four samples examined.Spores in the various images are numbered 1802, 1812, 1822, 1832, 1842,1852, 1862, 1942, 1952, and 1962. For the sake of clarity, only onespore is labeled per image.

It was found that samples exposed to ethanol/water solutions with lessthan 30% ethanol composition exhibited greater than 95% germination ofspores. In contrast, samples exposed to solutions with 30% or greaterethanol content, both with and without coating compositions dissolved inthe solution, exhibited less than 2% germination.

Example 16: Effect of Ethanol Concentration and Contact Time onPenicillium Spore Growth and Germination

20 μL droplets of spores of Penicillium spp. suspended in sterile waterat a concentration of ˜10⁵ spores/mL were deposited on top of microscopeslides coated with fruit wax. The spores were allowed to settle for 30minutes and the water droplet was aspirated off with a Kimwipe.

On top of the spore-treated slides was deposited 10 μL of a solution of0%, 30%, 70%, or 100% ethanol in deionized, sterile water; or 10 μL of70% or 100% ethanol solutions containing 10 mg/mL of2,3-dihydroxypropan-1-yl octadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate at a ratio of 30:70. After either 5 seconds, 10 seconds, 1minute, or 10 minutes, any remaining solvent was aspirated off with aKimwipe and a 20 μL droplet of sterile, deionized water was depositedonto each sample. The samples were incubated for 24 hours at 20° C. atapproximately 90% relative humidity, stained with lactophenol blue dye(diluted to 20% strength in sterile water), and imaged on a lightmicroscope. For each experimental condition, five samples were studied.

FIGS. 20A-20D and 21A-21B show representative microscope images (2000,2010, 2020, 2030, 2120, and 2130, respectively) of thePenicillium-coated slides after treatment with the compositionsdescribed above. FIG. 20A corresponds to treatment with water (0%ethanol). FIG. 20B corresponds to treatment with a 30% ethanol solution.FIG. 20C corresponds to treatment with a 70% ethanol solution. FIG. 20Dcorresponds to treatment with pure ethanol. FIG. 21A corresponds totreatment with a 70% ethanol solution containing 10 mg/mL of2,3-dihydroxypropan-1-yl octadecanoate and 1,3-dihydroxypropan-2-ylhexadecanoate at a ratio of 30:70. FIG. 21B corresponds to treatmentwith pure ethanol containing 10 mg/mL of 2,3-dihydroxypropan-1-yloctadecanoate and 1,3-dihydroxypropan-2-yl hexadecanoate at a ratio of30:70. Each image is representative of the other four samples examined.

FIG. 22 is a table showing percent germination of Penicillium spores foreach of the conditions described above. For 0 second solvent contacttime (control samples that were not treated with the solutions), greaterthan 85% germination of spores was observed on all samples. For 5 secondsolvent contact time, the samples treated with sterile DI water and 30%ethanol solution exhibited greater than 85% germination of spores, whilethe samples treated with 70% and 100% ethanol solutions (both with andwithout coating agents dissolved in the solutions) exhibited less than2% spore germination. For 10 second, 1 minute, and 10 minute solventcontact times, the samples treated with sterile DI water exhibitedgreater than 85% germination of spores, the samples treated with 30%ethanol solution exhibited about 60% germination of spores, and thesamples treated with 70% and 100% ethanol solutions (both with andwithout coating agents dissolved in the solutions) exhibited less than2% spore germination.

Various implementations of the compositions and methods have beendescribed above. However, it should be understood that they have beenpresented by way of example only, and not limitation. For example,solutions including any of the solutions including coating agentsdissolved in solvents described herein can also be applied to othersubstrates to sanitize the substrates and form protective coatings overthe substrates in a single application step. For example, the solutionscan be applied to meat, poultry, plants, textiles/clothing material, orother substrates, including non-edible substrates, in order to sanitizethe substrates and form a protective coating over the substrates in asingle application step. Where methods and steps described aboveindicate certain events occurring in certain order, those of ordinaryskill in the art having the benefit of this disclosure would recognizethat the ordering of certain steps may be modified and such modificationare in accordance with the variations of the disclosure. Theimplementations have been particularly shown and described, but it willbe understood that various changes in form and details may be made.Accordingly, other implementations are within the scope of the followingclaims.

1. (canceled)
 2. A method of treating an agricultural product,comprising: applying a mixture to a surface of the agricultural product,wherein the mixture comprises one or more monoacylglycerides and asolvent, and the solvent comprises at least 30% of an alcohol by volume;and at least partially removing the solvent from the surface of theagricultural product to yield a protective coating on the surface of theagricultural product, wherein the protective coating comprises the oneor more monoacylglycerides.
 3. The method of claim 2, wherein thesurface of the agricultural product comprises a cuticular layer of theagricultural product.
 4. The method of claim 2, wherein the one or moremonoacylglycerides comprise a compound of Formula I-B:

wherein: each R^(a) is independently —H or —C₁-C₆ alkyl; each R^(b) isindependently —H, —C₁-C₆ alkyl, or —OH; R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹,R¹² and R¹³ are each independently, at each occurrence, —H, —OR¹⁴,—NR¹⁴R¹⁵, —SR¹⁴, halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl,—C₃-C₇ cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl,alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted withone or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, or halogen; R³, R⁴, R⁷ and R⁸ areeach independently, at each occurrence, —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl, —C₃-C₇cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl,cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR¹⁴,—NR¹⁴R¹⁵, —SR¹⁴, or halogen; or R³ and R⁴ can combine with the carbonatoms to which they are attached to form a C₃-C₆ cycloalkyl, a C₄-C₆cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or R⁷ and R⁸ cancombine with the carbon atoms to which they are attached to form a C₃-C₆cycloalkyl, a C₄-C₆ cycloalkenyl, or 3- to 6-membered ring; R¹⁴ and R¹⁵are each independently, at each occurrence, —H, —C₁-C₆ alkyl, —C₂-C₆alkenyl, or —C₂-C₆ alkynyl; the symbol

represents an optionally single or cis or trans double bond; n is 0, 1,2, 3, 4, 5, 6, 7, or 8; m is 0, 1, 2, or 3; q is 0, 1, 2, 3, 4, or 5;and r is 0, 1, 2, 3, 4, 5, 6, 7, or
 8. 5. The method of claim 4, whereinthe compound of Formula I-B comprises:

or any combination thereof.
 6. The method of claim 4, wherein the one ormore monoacylglycerides further comprise a compound of Formula I-A:

wherein: each R^(a) is independently —H or —C₁-C₆ alkyl; each R^(b) isindependently —H, —C₁-C₆ alkyl, or —OH; R¹, R², R⁵, R⁶, R⁹, R¹⁰, R¹¹,R¹² and R¹³ are each independently, at each occurrence, —H, —OR¹⁴,—NR¹⁴R¹⁵, —SR¹⁴, halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl,—C₃-C₇ cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl,alkynyl, cycloalkyl, aryl, or heteroaryl is optionally substituted withone or more —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴, or halogen; R³, R⁴, R⁷ and R⁸ areeach independently, at each occurrence, —H, —OR¹⁴, —NR¹⁴R¹⁵, —SR¹⁴,halogen, —C₁-C₆ alkyl, —C₂-C₆ alkenyl, —C₂-C₆ alkynyl, —C₃—C₇cycloalkyl, aryl, or heteroaryl, wherein each alkyl, alkenyl, alkynyl,cycloalkyl, aryl, or heteroaryl is optionally substituted with —OR¹⁴,—NR¹⁴R¹⁵, —SR¹⁴, or halogen; or R³ and R⁴ can combine with the carbonatoms to which they are attached to form a C₃-C₆ cycloalkyl, a C₄-C₆cycloalkenyl, or 3- to 6-membered ring heterocycle; and/or R⁷ and R⁸ cancombine with the carbon atoms to which they are attached to form a C₃-C₆cycloalkyl, a C₄-C₆ cycloalkenyl, or 3- to 6-membered ring; R¹⁴ and R¹⁵are each independently, at each occurrence, —H, —C₁-C₆ alkyl, —C₂-C₆alkenyl, or —C₂-C₆ alkynyl; the symbol

represents an optionally single or cis or trans double bond; n is 0, 1,2, 3, 4, 5, 6, 7, or 8; m is 0, 1, 2, or 3; q is 0, 1, 2, 3, 4, or 5;and r is 0, 1, 2, 3, 4, 5, 6, 7, or
 8. 7. The method of claim 6, whereinthe compound of Formula I-A comprises:

or any combination thereof.
 8. The method of claim 2, wherein themixture further comprises a fatty acid, and the protective coatingfurther comprises the fatty acid.
 9. The method of claim 2, wherein themixture further comprises an organic salt, and the protective coatingfurther comprises the organic salt.
 10. The method of claim 2, whereinthe solvent comprises water.
 11. The method of claim 2, wherein thealcohol comprises ethanol, methanol, isopropanol or any combinationthereof.
 12. The method of claim 2, wherein the alcohol comprisesethanol.
 13. The method of claim 2, wherein the solvent comprises about50% to about 90% of the alcohol by volume.
 14. The method of claim 2,wherein the solvent comprises about 60% to about 90% of the alcohol byvolume.
 15. The method of claim 2, wherein the solvent comprises atleast 30% of ethanol by volume.
 16. The method of claim 2, wherein theagricultural product comprises a fruit or a vegetable.
 17. The method ofclaim 2, wherein applying the mixture to the surface of the agriculturalproduct reduces bacteria levels on the surface of the agriculturalproduct.
 18. The method of claim 17, wherein applying the mixturecomprises contacting the mixture and the surface of the agriculturalproduct for at least about 10 seconds.
 19. The method of claim 2,wherein the protective coating prevents or mitigates damage to theagricultural product caused by the alcohol.
 20. The method of claim 2,wherein the protective coating replaces or reinforces portions of theagricultural product that are damaged by the alcohol.
 21. The method ofclaim 2, wherein the protective coating reduces a rate of water lossfrom the produce.